Chloroacetyl chloride → 2-chloro-N-(3-(dibenzylamino)-2-hydroxypropyl)acetamide

HRID 57597Notes

Reaction equation

HRID 57597 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH2:7][CH:8]([OH:25])[CH2:9][N:10]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][CH2:7][CH:8]([OH:25])[CH2:9][N:10]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 104232791-Amino-3-(dibenzylamino)propan-2-ol

Product 1

HCID 117252152-chloro-N-(3-(dibenzylamino)-2-hydroxypropyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 2-chloroacetyl chloride (1.25 g, 10.96 mmol) in CHCl3 was added to the solution of 1-amino-3-(dibenzylamino)propan-2-ol (2.5 g, 9.26 mmol) in CHCl3 (50 mL) in ice-bath. The mixture was stirred for 1 hour, then stirred at room temperature for 2 hours. The organic layer concentrated, the residue was purified by column to give white solid.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. concentrationThe organic layer concentrated
  3. customthe residue was purified by column
  4. customto give white solid

Sources & evidence

ORD record
ord-e8137d1b78814b9a8d16fd8389767ed7
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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