Ethyl Bromide → HCID 68684613, compound

HRID 1992742Notes

Reaction equation

HRID 1992742 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[C:6]([N:8]([CH2:16][C:17]([CH3:25])=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)=[O:7].C(=O)(O)[O-].[Na+].[CH2:38](Br)[CH3:39]>ClCCl>[CH2:38]([N:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[CH2:10][CH2:9][N:8]([CH2:16][C:17]([CH3:25])=[CH:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:6](=[O:7])[C:5]1[CH:26]=[C:27]([O:31][CH3:32])[C:28]([O:29][CH3:30])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:39]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 516892Sodium BicarbonateHCID 68680565HCID 68680565, compound

Product 1

HCID 68684613HCID 68684613, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4,5-trimethoxy-N-(2-methyl-3-phenyl-allyl)-N-(2-pyrrolidin-2-yl-ethyl)-benzamide 0.1 g (2.28 mmol) in dry dichloromethane 5 ml, sodium bicarbonate 0.01 g (2.7 mmol) was added followed by ethyl bromide 0.037 g (3.4 mmol) at 0° C. The reaction mixture was stirred at room temperature for 14 hrs. Inorganics were filtered off and filtrate was concentrated. Crude material was subjected to column chromatography on silica gel, elution with chloroform-methanol to yield desired compound as a free amine. This was converted to its hydrochloride salt 42 mg as a yellow semi-solid.

Workup

  1. filtrationInorganics were filtered off
  2. concentrationfiltrate was concentrated
  3. washCrude material was subjected to column chromatography on silica gel, elution with chloroform-methanol

Sources & evidence

ORD record
ord-e08964a0a2364eda981ee0cd741b86d0
Source dataset
uspto-grants-2010_01
Patent number
US07649011B2

Reaction notes

Loading…