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

HRID 1057404Notes

Reaction equation

HRID 1057404 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].C(Cl)[Cl:23]>>[ClH:23].[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 hydrochlorideYield 100%

Procedure

Trimethylsilyl cyanide (TMSCN) (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 methylene chloride (15 mL) under argon atmosphere. After 15 h, 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 1M HCl in ether (33 mL) was added dropwise to give the title compound (6.60 g, 100%) as an off-white crystalline precipitate. mp: 137-138° C.; 1H-NMR (300 MHz, CD3OD) δ 7.31-7.48 (m, 5H), 5.32 (s, 2H), 4.68 (q, J=7.0 Hz, 1H), 4.22 (s, 2H), 1.73 (d, J=7.1 Hz, 3H); 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 1M HCl in ether (33 mL) was added dropwise

Sources & evidence

ORD record
ord-3870593d511542c9ac0d4b4a3218eac1
Source dataset
uspto-grants-2003_02
Patent number
US06514978B2

Reaction notes

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