4-Methyloxybenzyl chloride → HCID 22100941, compound

HRID 1457812Notes

Reaction equation

HRID 1457812 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.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=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]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[CH2:15][CH:16]=1

Participants

3

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 22100972HCID 22100972, compound

Product 1

HCID 22100941HCID 22100941, compoundYield 4.18%

Procedure

4-(Benzothiophen-2-yl)-1,2,3,6-tetrahydropyridine hydrochloride (250 mg, 0.99 mmol) was reacted with 4-methoxybenzyl chloride (0.13 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 158°-160° C. (Found: C, 75.09; H, 5.05; N, 4.31; C21 H21NOS requires C, 75.19; H, 6.31; N, 4.18%). δH (CDCl3) 2.65 (2H, m, NCH2CH2), 2.74 (2H, m, NCH2 CH2), 3.20 (2H, m, NCH2CH2), 3.61 (2H, s, NCH2Ar), 3.81 (3H, s, OMe), 6.18 (1H, m, NCH2CH), 6.87 (2H, d, J 8.6Hz, ArH), 7.12 (1H, s, ArH), 7.28 (4H, m, ArH), 7.65 (1H, d, J 6.8Hz, ArH), 7.73 (1H, d, J 6.9Hz, ArH). m/z (ES+) 336 (M+1)+.

Workup

  1. customThe crude product was triturated with hot methanol

Sources & evidence

ORD record
ord-0cc9f0c88b474dd2bb229f1e0b49082c
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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