Dimethylformamide → methyl N-[phenyl(2-pyridinyl)methyl]glycine

HRID 622308Notes

Reaction equation

HRID 622308 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:16][C:17]([O:19]C)=[O:18].[CH2:21](N(CC)CC)C.CN(C)C=O>O>[CH3:21][N:8]([CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7295Methyl chloroacetateHCID 8471TriethylamineHCID 2775258Phenyl(pyridin-2-yl)methanamine

Product 1

HCID 65056421methyl N-[phenyl(2-pyridinyl)methyl]glycineYield 62.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 44 parts of α-phenyl-2-pyridinemethanamine, 27 parts of methyl chloroacetate, 30 parts of N,N-diethylethanamine and 270 parts of N,N-dimethylformamide was stirred overnight at room temperature. The reaction mixture was poured into 1000 parts of water. The product was extracted with 1,1'-oxybisethane. The extract was washed three times with water, dried, filtered and evaporated, yielding 37 parts (62.8%) of methyl N-[phenyl(2-pyridinyl)methyl]glycine as a residue.

Workup

  1. extractionThe product was extracted with 1,1'-oxybisethane
  2. washThe extract was washed three times with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d256f2aaacfc427f8fb0b2c95104933f
Source dataset
uspto-grants-1988_09
Patent number
US04770689

Reaction notes

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