1-(Bromomethyl)-4-chlorobenzene → HCID 10359942, compound

HRID 1457815Notes

Reaction equation

HRID 1457815 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.[Cl: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[N:4]=[C:3]1[C:11]1[CH2:12][CH2:13][N:14]([CH2:22][C:21]2[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=2)[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 22100974HCID 22100974, compound

Product 1

HCID 10359942HCID 10359942, compoundYield 60.1%

Procedure

4-(Benzothiazol-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (520 mg, 2 mmol) was reacted with 4-chlorobenzyl bromide (507 mg, 2.4 mmol) as exemplified in Example 1. The crude product was recrystallised from dichloromethane and methanol to afford the title compound as a yellow solid (410 mg, 60%); (Found: C, 66.70; H, 4.87; N, 8.16. C19H17ClN2S requires C, 66.95; H, 5.03; N, 8.22%). δH (CDCl3), 2.74 (2H, m, NCH2CH2), 2.83 (2H, m, NCH2 CH2), 3.22 (2H, m, NCH2CH2), 3.63 (2H, s, NCH2Ar), 6.67 (1H, m, NCH2CH), 7.31 (4H, s, ArH), 7.34 (1H, d of t, J 8.1Hz, J 1.2Hz, ArH), 7.44 (1H, d of t, J 7.4Hz, J 1.2Hz, ArH), 7.82 (1H, d, J 7.8Hz, ArH), 7.97 (1H, d, J 8.1Hz, ArH). m/z (ES+) 341 (M+1)+.

Workup

  1. customThe crude product was recrystallised from dichloromethane and methanol

Sources & evidence

ORD record
ord-3dce740b914f431eabbc3b28d91e4eed
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

Loading…