Bromomethylcyclopropane → HCID 54381315, compound

HRID 487121Notes

Reaction equation

HRID 487121 reaction equation
[CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4][NH:3][CH2:2]1.Br[CH2:16][CH:17]1[CH2:19][CH2:18]1>ClCCl>[CH:17]1([CH2:16][N:3]2[CH2:2][CH2:1][C@@H:10]3[C@H:5]([CH2:6][CH2:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=43)[CH2:4]2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 54260071HCID 54260071, compound

Product 1

HCID 54381315HCID 54381315, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.200 g (1.07 mmol) of trans-1,2,3,4,4a,5,6,10b-octahydrobenz[f]isoquinoline in anhydrous dichloromethane (20 ml) was added 0.200 g (1.48 mmol) of (bromomethyl)cyclopropane and the reaction mixture was left to stand for 24 h. The solvent was removed in vacuo and the residue was chromatographed on flash silica, eluting with 10% methanol/dichloromethane to give 0.160 g (62%) of the title product as an oil. The hydrochloride salt was made using etheral hydrogen chloride. Upon evaporation of the solvent, washing with ether and recrystallisation from ethanol/ethyl acetate/petroleum ether, the title product hydrochloride was obtained as a white sold, m.p. 255°-257° C. NMR δ(D2O) 0.43 (2H, m), 0.78 (2H, m), 1.17 (1H, m), 1.58 (1H, m), 1.80-1.94 (2H, m), 2.67-2.77 (2H, m), 2.90-2.97 (3H, m), 3.09 (2H, d, J=7.4 Hz), 3.20 (1H, t of d, J=13.1 and 3.0 Hz), 3.74 (1H, m), 3.87 (1H, m), 7.22-7.31 (3H, m), 7.36-7.38 (1H, m). m/z (CI+, NH3) 242 (M+H)+, 182, 165.

Workup

  1. waitthe reaction mixture was left
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed on flash silica
  4. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-6aa0d11dc59a4f558558ea6124aa3e07
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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