Pyridine → 5-(4-Fluorophenyl)-3-(2-piperidinyl)pyridine fumarate

HRID 1941272

반응식

HRID 1941272 반응식
N1C=CC=CC=1.[C:7]([OH:14])(=[O:13])/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)[CH:25]=[N:26][CH:27]=2)=[CH:18][CH:17]=1>CO>[C:7]([OH:14])(=[O:13])/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11].[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[C:24]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)[CH:25]=[N:26][CH:27]=2)=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 444972Fumaric AcidHCID 196942955-(4-Fluorophenyl)-3-(2-piperidinyl)pyridine

생성물 1

HCID 196942945-(4-Fluorophenyl)-3-(2-piperidinyl)pyridine fumarate수율 70%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The above described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether resulted in the formation of 5-(4-fluorophenyl)-3-(2-piperidinyl)pyridine fumarate (70%) as a colorless solid. M.p. 209°-210° C. (decomp., Et2O); 1H NMR (DMSO-d6, 300 MHz): δ8.86 (s, 1H), 8.63 (s, 1H), 8.32 (s, 1H), 7.81 (dd, J=8, 5 Hz, 2H), 7.32 (app. t, J=8 Hz, 2H), 6.49 (s, 2H), 4.24 (dd, J=10, 4 Hz, 1H), 3.37 (d, J=12 Hz, 1H), 2.97 (m, 1H), 1.5-2.1 (m, 6H).

후처리

  1. customAfter 30 minutes the solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-5c3a392575c94d0784d5f79e36edb4d8
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703100

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