Furan, 2-(bromomethyl)tetrahydro- → HCID 18607205, compound

HRID 542219Notes

Reaction equation

HRID 542219 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-].[Na+].[CH2:29](Br)[CH:30]1[O:34][CH2:33][CH2:32][CH2:31]1>ClCCl.CN(C)C=O>[CH3:2][N:3]([C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1[N:22]([CH3:23])[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][O:34]1)[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

6

Reactant 3

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 516892Sodium Bicarbonate2×HCID 18607203HCID 18607203, compound

Product 1

HCID 18607205HCID 18607205, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of trans-(±)-N-methyl-N-[2-(methylamino)cyclohexyl]benzo[b]thiophene-4-acetamide monohydrochloride (120 mg, 0.34 mmol) in dichloromethane (10 ml) was treated with saturated aqueous sodium bicarbonate to liberate the parent amine. The oil was dissolved in dimethyl formamide and treated with tetrahydrofurfuryl bromide (68 mg, 0.41 mmol) and sodium bicarbonate (43 mg, 0.5 mmol). The resulting mixture was stirred in an oil bath at 95°-110° C. for 20 hours then concentrated in vacuo, poured into saturated aqueous sodium bicarbonate (15 ml) and extracted with dichloromethane (2×15 ml). Silica gel chromatography (70:30:1 ethyl acetate-hexanetriethylamine) furnished trans-(±)-N-methyl-N-(2-(methyl[(tetrahydro-2-furanyl)methyl]amino)cyclohexyl)benzo[b]thiophene-4-acetamide as a colourless oil (43 mg, 32%); m/e: 400 (M+), 329, 286, 195, 147; t.l.c. analysis of this product (50:50:1 ethyl acetate-hexane-triethylamine, multiple development) indicated that it consisted of two components.

Workup

  1. concentrationthen concentrated in vacuo
  2. additionpoured into saturated aqueous sodium bicarbonate (15 ml)
  3. extractionextracted with dichloromethane (2×15 ml)

Sources & evidence

ORD record
ord-906d458400474864b809acee87f8697c
Source dataset
uspto-grants-1987_04
Patent number
US04656182

Reaction notes

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