1-(Bromomethyl)-3-chlorobenzene → HCID 15337060, compound

HRID 1457809Notes

Reaction equation

HRID 1457809 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br>>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]1[CH2:12][CH2:13][N:14]([CH2:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[CH:19]=2)[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 22100972HCID 22100972, compound

Product 1

HCID 15337060HCID 15337060, compoundYield 15%

Procedure

4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was reacted with 3-chlorobenzyl bromide (0.2 ml, 1.5 mmol) as exemplified in Example 1. The crude product was triturated with methanol to give the title compound as a pale yellow solid (50 mg, 15%); (Found: C, 69.05; H, 5.03; N, 4.07. C20H18ClNS. 0.5H2O requires C, 68.85; H, 5.49; N, 4.01%). δH (CDCl3), 2.65 (2H, m, NCH2CH2), 2.73 (2H, m, NCH2CH2), 3.18 (2H, m, NCH2CH2), 3.62 (2H, s, NCH2Ar), 6.19 (1H, m, NCH2 CH), 7.12 (1H, s, ArH), 7.28 (5H, m, ArH), 7.39 (1H, s, ArH), 7.67 (1H, d of d, J 6.2Hz, J 1.9Hz, ArH), 7.73 (1H, d of d, J 8.4Hz, J 1.8Hz, ArH). m/z (ES+) 340 (M+1)+.

Workup

  1. customThe crude product was triturated with methanol

Sources & evidence

ORD record
ord-900a1bd5ec5e46f2b90111e832babf4f
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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