Acetaldehyde → Benzyl-N-(1-cyanoethyl)glycine hydrochloride

HRID 1016254

Reaction equation

HRID 1016254 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH2:7]([NH:14][CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:19](=O)[CH3:20].[Cl:22]CCl>>[ClH:22].[CH2:7]([N:14]([CH:19]([C:5]#[N:6])[CH3:20])[CH2:15][C:16]([OH:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 177AcetaldehydeHCID 6344DichloromethaneHCID 82115Trimethylsilyl cyanideHCID 869652-(Benzylamino)acetic acid

Product 1

HCID 68560147Benzyl-N-(1-cyanoethyl)glycine hydrochloride

Procedure

Trimethylsilyl cyanide (4.0 mL, 30 mmol) was added cautiously to a stirred solution of benzyl glycine free base (5.0 g, 30 mmol) and acetaldehyde (1.7 mL, 30 mmol) in dichloromethane (15 mL) under argon atmosphere. After 15 hours, the volatile components were removed in vacuo, and the residue was dissolved in ethyl acetate (200 mL), washed with brine (100 mL), dried (Na2SO4) and evaporated to an oil. The oil was redissolved in ether (30 mL) and ethanol (30 mL), and 1 M HCl in ether (33 mL) was added dropwise to give the title compound as an off-white crystalline precipitate (6.60 g, 100%). mp: 137-138° C. 1H NMR (CD3OD) δ 7.31-7.48 (m, 5H), 5.32 (s, 2H), 4.68 (q, 1H, J=7.0 Hz), 4.22 (s, 2H), 1.73 (d, 3H, J=7.1 Hz). CI MS m/z=192 (M+H). Anal. Calcd. for C12H14N2O2.HCl: C, 56.49; H, 5.95; N, 11.00. Found: C, 56.32; H, 5.88; N, 10.89.

Workup

  1. customthe volatile components were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated to an oil
  6. dissolutionThe oil was redissolved in ether (30 mL)
  7. additionethanol (30 mL), and 1 M HCl in ether (33 mL) was added dropwise

Sources & evidence

ORD record
ord-013c8dd70bc64e8d96ba972bcfd53ea5
Source dataset
uspto-grants-2002_11
Patent number
US06476016B2

Linked notes

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