In a large mixing bowl stir together 1-1/4 cups of the flour, the yeast, and cinnamon; set aside.
In a medium saucepan heat and stir water, sugar, cooking oil, and salt just until warm (120 degrees F to 130 degrees F). Add oil mixture to flour mixture; add egg and vanilla. Beat with an electric mixer on low to medium speed for 30 seconds, scraping the sides of the bowl constantly. Beat on high speed for 3 minutes. Using a wooden spoon, stir in as much of the remaining flour as you can.
Turn dough out onto a lightly floured surface. Knead in enough of the remaining flour to make a moderately soft dough that is smooth and elastic (3 to 5 minutes total). Shape dough into a ball. Place in a lightly greased bowl, turning once to grease the surface of the dough. Cover and let rise in a warm place until double in size (about 1 hour).
Punch dough down. Turn dough out onto a lightly floured surface. Divide in half. Cover and let rise for 10 minutes.
Roll dough, 1 portion at a time, to 1/4-inch thickness. Cut dough with a floured 1-1/2-inch biscuit cutter, dipping cutter into flour between cuts. Place about 1/4 teaspoon chocolate spread onto the centers of half of the circles. Lightly moisten edges of circles; top with remaining circles. Press edges together to seal. Repeat with remaining dough and fillings. Reroll and cut trimmings.
Fry filled doughnuts, 3 or 4 at a time, in deep hot oil (365 degrees F) about 1 minute on each side or until golden, turning once with a slotted spoon. Remove from oil; drain on paper towels. Sprinkle with powdered sugar. Cool on wire racks.
Makes about 42 mini-sufganyot. Nutrition facts are given per sufganyot.