Chloroacetyl chloride → HCID 14851587, compound

HRID 329442Notes

Reaction equation

HRID 329442 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>ClCCl>[Cl:19][CH2:20][C:21]([N:9]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:8])[CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:22]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 14851585HCID 14851585, compound

Product 1

HCID 14851587HCID 14851587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.0 g of N-(2,6-dimethylphenyl)-3-pyridinepropanamine in 75 ml of dichloromethane was added dropwise to a cold (0° C.) solution of 3.5 ml of chloroacetylchloride in 35 ml of dichloromethane. The cooling bath was removed and the reaction was allowed to warm to room temperature over 30 minutes followed by the addition of excess aqueous sodium bicarbonate solution. The layers were separated and the organic layer was washed with brine, dried with sodium sulfate and evaporated to give 13.4 g of product as a dark oil which was used directly in the next steps, that is, in Examples 20 and 21.

Workup

  1. customThe cooling bath was removed
  2. additionfollowed by the addition of excess aqueous sodium bicarbonate solution
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-604cc82342a3457dae406c8e7ae597fb
Source dataset
uspto-grants-1990_01
Patent number
US04891429

Reaction notes

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