alpha-Bromo-o-chlorotoluene → HCID 15337061, compound

HRID 1457810Notes

Reaction equation

HRID 1457810 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:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]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]([CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[Cl:17])[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 11905alpha-Bromo-o-chlorotolueneHCID 22100972HCID 22100972, compound

Product 1

HCID 15337061HCID 15337061, compoundYield 12%

Procedure

4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was reacted with 2-chlorobenzyl bromide (0.24 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 brown solid (40 mg, 12%) m.p. 105°-106° C.; (Found: C, 69.29; H, 5.17; N, 4.23. C20 H18ClNS. 0.5H2O requires C, 68.85; H, 5.49; N, 4.01%). δH (CDCl3), 2.66 (2H, m, NCH2CH2), 2.80 (2H, m, NCH2CH2), 3.27 (2H, m, NCH2CH2), 3.77 (2H, s, NCH2Ar), 6.20 (1H, m, NCH2CH), 7.13 (1H, s, ArH), 7.25 (4H, m, ArH), 7.36 (1H, d of d, J 7.7Hz, J 1.4Hz, ArH), 7.53 (1H, d of d, J 7.5Hz, J 1.6Hz, ArH), 7.66 (1H, d of d, J 6.9Hz, J 1.5Hz, ArH), 7.73 (1H, d of d, J 8.7Hz, J 1.7Hz, ArH). m/z (ES+) 340 (M+1)+.

Workup

  1. customThe crude product was triturated with methanol

Sources & evidence

ORD record
ord-0b04b1bc137c465780d4d2139803bf68
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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