Potassium Carbonate → HCID 23294523, compound

HRID 1955189Notes

Reaction equation

HRID 1955189 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.[O:17]([CH2:24][CH2:25][CH2:26][Br:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>>[BrH:27].[O:1]=[C:2]1[N:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:26][CH2:25][CH2:24][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11][CH2:12]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one

Product 1

HCID 23294523HCID 23294523, compoundYield 54.4%

Procedure

A mixture of 4-(2-keto-1-benzimidazolinyl)piperidine (980 mg. 4.51 mmol) and 3-phenoxypropyl bromide (1.02 g, 4.73 mmol) was reacted in the presence of K2CO3 in CH2CN by refluxing under N2 for about 4 h to obtain the hydrobromide as a pale beige solid (1.06 g, 54%); mp 136-138° C. (foams); 1H NMR (CD3OD) δ 2.12 (d, J=13 Hz, 2H), 2.25-2.40 (m, 2 H), 2.81-2.99 (m, 2 H), 3.22-3.49 (m, 4 H), 3.82 (d, J=12 Hz, 2 H), 4.14 (t, J=8.4 Hz, 2 H), 4.55-4.70 (m, 1 H), 6.91-7.41 (m, 9 H).

Workup

  1. temperatureby refluxing under N2 for about 4 h

Sources & evidence

ORD record
ord-973821d0e2664a31922dc20057c61515
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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