Dimethylformamide dimethyl acetal → HCID 13375846, compound

HRID 1979637Notes

Reaction equation

HRID 1979637 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[CH3:17][N:18]([CH3:20])[CH:19]=[N:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 13375846HCID 13375846, compoundYield 83.2%

Procedure

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.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureto cool overnight
  3. concentrationconcentrated in vacuo to the product (15.5 g of oil, 83.2% yield), which
  4. customA small portion crystallizes from hexane
  5. customto afford colorless needles with a melting point of 61°-65° C.

Sources & evidence

ORD record
ord-edfa9d44bc0442849eaaf302b658b2a6
Source dataset
uspto-grants-1984_11
Patent number
US04481360

Reaction notes

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