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Pyridine → N-benzyl-N-methyl-2(S)-(3,4-dichlorophenyl)-4-pentenoamide

HRID 1647706
Notes
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Reaction equation

HRID 1647706 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:13][CH:14]=[CH2:15])[C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)(=O)C(Cl)=O.[CH2:22]([NH:29][CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[CH2:22]([N:29]([CH3:30])[C:10](=[O:12])[C@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:13][CH:14]=[CH2:15])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 7669N-MethylbenzylamineHCID 65578Oxalyl chlorideHCID 15261879(S)-2-(3,4-dichlorophenyl)pent-4-enoic acid

Product 1

HCID 15288290N-benzyl-N-methyl-2(S)-(3,4-dichlorophenyl)-4-pentenoamide

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.8 g (19.6 mmol) of 2-(S)-(3,4-dichlorophenyl)-4-pentenoic acid in 50 mL of CH2Cl2 and 10 drops of DMF was cooled in an ice bath and 1.8 mL of oxalyl chloride was added. The solution was stirred for 15 min after gas evolution had ceased. The mixture was concentrated in vacuo and the residue was diluted with 50 mL of CH2Cl2. The solution was cooled in ice bath as 2.6 mL (20.4 mmol) of N-benzyl-methyl amine and 1.7 mL (21 mmol) of pyridine were added. After stirring for 1 h at ice bath temperature the solution was diluted with CH2Cl2 and washed with water, 1.2N HCl and brine. The solution was dried over Na2SO4 and concentrated to give N-benzyl-N-methyl-2(S)-(3,4-dichlorophenyl)-4-pentenoamide as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was diluted with 50 mL of CH2Cl2
  3. additionwere added
  4. stirringAfter stirring for 1 h at ice bath temperature the solution
  5. washwashed with water, 1.2N HCl and brine
  6. dry with materialThe solution was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee4b5f70583b49ca9a142d52169ab810
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05434158

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes