Dimethylformamide → N-[3-(4-oxo-piperidino)-propyl]-benzimidazolone

HRID 2198756Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].[C:15](=O)(O)[O-].[Na+].[O:20]1[CH2:24][CH2:23][CH2:22]C1.C[N:26]([CH3:29])C=O>>[O:20]=[C:24]1[CH2:15][CH2:29][N:26]([CH2:2][CH2:3][CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[NH:7][C:6]2=[O:14])[CH2:22][CH2:23]1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 8028Tetrahydrofuran

HCID 516892Sodium Bicarbonate

HCID 18104191-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 13056043N-[3-(4-oxo-piperidino)-propyl]-benzimidazoloneYield 39%

Procedure

A mixture of 6.3 gm of N-(3-chloropropyl)-benzimidazolone, 4.6 gm of 4-piperidine hydrochloride monohydrate, 5.0 gm of sodium bicarbonate, 50 ml of tetrahydrofuran, and 50 ml of dimethylformamide, was heated to reflux, for 36 hours. The product was worked up as usual, yielding 3.2 gm (39% of theory) of N-[3-(4-oxo-piperidino)-propyl]-benzimidazolone, m.p. 134°-136° C.

Workup

temperaturewas heated
temperatureto reflux, for 36 hours

Sources & evidence

ORD record: ord-c7cda93a885741f5b525aa2c0befd1ea
Source dataset: uspto-grants-1982_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04359468

Reaction notes

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