Allyl bromide → HCID 13911095, compound

HRID 542217Notes

Reaction equation

HRID 542217 reaction equation
Cl.[CH3:2][N:3]([C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[NH:22][CH3:23])[C:4](=[O:15])[CH2:5][C:6]1[C:14]2[CH:13]=[CH:12][S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](N(CC)CC)[CH3:31].[CH2:37](Br)C=C>ClCCl.C(O)C>[CH3:2][N:3]([C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[N:22]([CH3:37])[CH2:23][CH:30]=[CH2:31])[C:4](=[O:15])[CH2:5][C:6]1[C:14]2[CH:13]=[CH:12][S:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 18607203HCID 18607203, compound

Product 1

HCID 13911095HCID 13911095, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of trans-(±)-N-methyl-N-[2-(methylamino)cyclohexyl]benzo[b]thiophene-4-acetamide monohydrochloride (400 mg, 1.13 mmol) in dichloromethane (10 ml) was treated with aqueous potassium carbonate (30 ml) to liberate the parent amine. This oil was dissolved in ethanol (10 ml), dichloromethane (1 ml) and triethylamine (0.3 ml, 2.2 mmol) and treated with allyl bromide (257 mg, 2.1 mmol). This mixture was stirred in an oil bath at 50°-60° C. for six hours, concentrated in vacuo and partitioned between 10% aqueous potassium carbonate and dichloromethane. The organic fractions furnished an oil which after silica gel chromatography (100:1 ethyl acetate-triethylamine) gave trans-(±)-N-methyl-N-(2-[methyl(2-propenyl)amino]cyclohexyl)benzo[b]thiophene-4-acetamide (270 mg, 67%); δH (CDCl3) 6.0-4.3 (3H, m); Vmax (liquid film) 1637 cm-1.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between 10% aqueous potassium carbonate and dichloromethane
  3. customThe organic fractions furnished an oil which after silica gel chromatography (100:1 ethyl acetate-triethylamine)

Sources & evidence

ORD record
ord-9c411db21bea42ec849ad90297f53947
Source dataset
uspto-grants-1987_04
Patent number
US04656182

Reaction notes

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