Ammonia → 2-(4-Benzyloxy-1,2,3,6-tetrahydropyridin-1-ylmethyl)benzimidazole

HRID 861380Notes

Reaction equation

HRID 861380 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.N>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH2:10][CH2:11][N:12]([CH2:16][C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 785712-ChloromethylbenzimidazoleHCID 123288284-(Benzyloxy)pyridine

Product 1

HCID 97971092-(4-Benzyloxy-1,2,3,6-tetrahydropyridin-1-ylmethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared from 4-benzyloxy pyridine and 2-(chloromethyl) benzimidazole in an analagous manner to that described previously. M.p. 170°-172° C. (PhMe); (Found: C, 75.19; H, 6.45; N, 13.02. C20H21N3O requires C, 75.21; H, 6.63; N, 13.16%). δH (CDCl3) 2.35 (2H, br s, tetrahydropyridinyl 3-CH2), 2.81 (2H, t, J 5.6 Hz, tetrahydropyridinyl 2-CH2), 3.21 (2H, br s, tetrahydropyridinyl 6-CH2), 3.98 (2H, s, NCH2Ar), 4.75 (1H, br s, tetrahydropyridinyl 5-CH), 4.81 (2H, s, PhCH2O), 7.22-7.27 (3H, m, ArH), 7.31-7.37 (6H, m, ArH), and 7.56 (1H, br s, NH); m/z (CI+, NH3), 336 (M+NH4)+.

Sources & evidence

ORD record
ord-48c417010f0d4a3d9cb3e843b7b380d0
Source dataset
uspto-grants-1998_02
Patent number
US05714498

Reaction notes

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