Dihydrouracil → 3-(3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-5,6-dihydro-2,4(1H,3H)-pyrimidinedione hydrochloride

HRID 342603Notes

Reaction equation

HRID 342603 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH2:7][CH2:6]1.[NH:24]1[CH2:29][CH2:28][C:27](=[O:30])[NH:26][C:25]1=[O:31]>>[ClH:1].[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][N:26]3[C:27](=[O:30])[CH2:28][CH2:29][NH:24][C:25]3=[O:31])[CH2:6][CH2:7]2)=[C:12]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH:13]=1

Participants

3

Reactant 2

HCID 649DihydrouracilHCID 702021591-Chloro-3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propane

Product 1

HCID 702026393-(3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-5,6-dihydro-2,4(1H,3H)-pyrimidinedione hydrochloride

Procedure

substituting 1-chloro-3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propane and 5,6-dihydro-2,4(1H,3H)-pyrimidinedione and recrystallizing from a solution of hydrochloric acid in alcohol gave 3-(3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propyl)-5,6-dihydro-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 186°-189° C.; Anal.: Calcd. for C19H24F4N5O3.(HCl)2 : C, 44.10; H, 5.06; N, 10.83%; Found: C, 43.99; H, 5.16; N, 10.78%; and

Workup

  1. customrecrystallizing from a solution of hydrochloric acid in alcohol

Sources & evidence

ORD record
ord-523a918aec9847d5b874556682660983
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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