(S)-1-Phenylbutylamine → (S)-2-cyano-N-(1-phenylbutyl)acetamide

HRID 2406589Notes

Reaction equation

HRID 2406589 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14](OCCN(CC)CC)=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2].C1([C@@H](N)CCC)C=CC=CC=1>>[C:1]([CH2:3][C:4]([NH:6][C@H:7]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:8][CH2:9][CH3:10])=[O:5])#[N:2]

Participants

3

Reactant 2

HCID 2449444(S)-1-PhenylbutylamineHCID 668220192-Cyano-N-(1-(4-(2-(diethylamino)ethoxy)phenyl)butyl)acetamide

Product 1

HCID 66822152(S)-2-cyano-N-(1-phenylbutyl)acetamideYield 58%

Procedure

The title compound was prepared by using a similar procedure as described for the preparation of 29 except that (S)-1-phenylbutylamine was used instead of 1-(4-(2-(diethylamino)ethoxy)phenyl)butan-1-amine (25). This produced crude product which was purified by flash silica gel column chromatography, eluting with 7:3 hexanes/ethyl acetate, to give 39 (375 mg, 58%) as a white solid: MS (ES+) m/z 217.1.1 (M+H)+.

Workup

  1. customThe title compound was prepared
  2. customThis produced crude product which
  3. customwas purified by flash silica gel column chromatography
  4. washeluting with 7:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2bbccb3301ad4c8a967df9b2b3cdb307
Source dataset
uspto-grants-2014_08
Patent number
US08809377B2

Reaction notes

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