4-Fluorobenzyl bromide → HCID 22100952, compound

HRID 1457811Notes

Reaction equation

HRID 1457811 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.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>>[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]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([F:17])=[CH:19][CH:20]=2)[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 22100972HCID 22100972, compound

Product 1

HCID 22100952HCID 22100952, compoundYield 4.3%

Procedure

4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was reacted with 4-fluorobenzyl bromide (0.12 ml, 0.99 mmol) as exemplified in Example 1. The crude product was triturated with hot methanol to give the title compound as a pale yellow solid mp 142°-144° C. (Found: C, 73.78; H, 5.57; N, 4.36. C20 H18FNS. 0.1H2O requires C, 73.86; H, 5.64; N, 4.30%). δH (CDCl3) 2.64 (2H, m, NH2CH2), 2.72 (2H, m, NCH2CH2), 3.18 (2H, m, NCH2CH2), 3.61 (2H, s, NCH2Ar), 6.19 (1H, m, NCH2CH), 7.02 (2H, t, J 8.6Hz, ArH), 7.12 (1H, s, ArH), 7.30 (4H, m, ArH), 7.67 (1H, d of d, J 6.7Hz, ArH), 7.73 (1H, d of d, J 6.8Hz, ArH). m/z (ES+) 324 (M+1)+.

Workup

  1. customThe crude product was triturated with hot methanol

Sources & evidence

ORD record
ord-7dde0a2027a742fdb4437d9a8d9de25f
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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