Dimethylformamide dimethyl acetal → HCID 13375846, compound

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Reaction Steps

The starting 4-amino-1-benzylpiperidine from Part B above (15.0 g, 78.8 mmol) is treated with dimethylformamide dimethylacetal (18.78 g, 157.6 mmol) and refluxed for 2 hours. The solution is permitted to cool overnight, then concentrated in vacuo to the product (15.5 g of oil, 83.2% yield), which solidifies on standing. A small portion crystallizes from hexane to afford colorless needles with a melting point of 61°-65° C.: NMR (CDCl3 δ) 7.28, 3.49, 2.80, and 1.75-3.0; mass spectral molecular ion peak at m/e 245, with abundant fragment ions at m/e 200, 173, 172, 154, and 91.

Provenance & Evidence