Hydrochloric Acid → 4-Benzyl-1-(2-(2-oxobenzimidazol-5-oxy)ethyl)-1,2,5,6-tetrahydropyridine

HRID 1955235Notes

Reaction equation

HRID 1955235 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8]Br)=[CH:4][C:3]=1[N+:12]([O-])=O.[CH2:15]([C:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:28]([O-])([O-])=[O:29].[K+].[K+].Cl>>[CH2:15]([C:22]1[CH2:27][CH2:26][N:25]([CH2:8][CH2:7][O:6][C:5]2[CH:10]=[CH:11][C:2]3=[N:1][C:28](=[O:29])[N:12]=[C:3]3[CH:4]=2)[CH2:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136327214-Benzyl-1,2,5,6-tetrahydropyridineHCID 154854442-(4-Amino-3-nitrophenoxy)ethyl bromide

Product 1

HCID 232942204-Benzyl-1-(2-(2-oxobenzimidazol-5-oxy)ethyl)-1,2,5,6-tetrahydropyridine

Procedure

The title compound was prepared from (4-amino-3-nitrophenoxy)ethyl bromide (1.31 g, 5.0 mmol), 4-benzyl-1,2,5,6-tetrahydropyridine (870 mg, 5.02 mmol), K2CO3 (700 g) and KI (80 mg) in three steps as a slightly grey powder, mp. 202-3° C. 1H NMR (DMSO-d6): 1.952 (bs, 2H), 2.50-2.56 (m, 4H), 2.686 (t, 2H, J=6), 2.973 (bs, 2H), 3.241 (s, 2H), 3.988 (t, 2H, J=6), 5.381 (s, 1H), 6.48-6.50 (m, 2H), 6.768 (d, 1H, J=9), 7.14-7.30 (m, 5H). The hydrochloride, mp. 256-7° C. Analysis, Calcd. for (C21H24ClN3O2 +0.2 HCl): C 64.44, H 6.12, N 10.61; Found: C 64.15, H 6.20, N 10.68.

Sources & evidence

ORD record
ord-e3d782120f024046a90d6f611a36427e
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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