Dimethylformamide → HCID 14848506, compound

HRID 1608363Notes

Reaction equation

HRID 1608363 reaction equation
[CH:1]([NH2:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:1]([NH:14][CH2:16][CH2:17][CH2:18][Cl:19])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7036BenzhydrylamineHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 14848506HCID 14848506, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 0.1 mole of benzhydrylamine, 39.3 g (0.25 moles) of 1-bromo-3-chloropropane, 13.8 g (0.1 mole) of potassium carbonate, 20.0 ml of dimethylformamide and 20.0 ml of water were heated at 75° C. for 2 hr. The organic layer was separated and concentrated on a rotary high vacuum evaporator to give 26 g of title compound of 85-90% purity of title compound containing about 5% each of benzhydrylamine and 1-benzhydrylazetidine.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated on a rotary high vacuum evaporator

Sources & evidence

ORD record
ord-d002cac330034a2b81ea17ecf0205735
Source dataset
uspto-grants-1989_09
Patent number
US04870189

Reaction notes

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