Hydrochloric Acid → 3-(4-Fluorophenacyl)piperidine, maleate salt

HRID 1657833노트

반응식

HRID 1657833 반응식
N#CBr.C[N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])[CH2:6]1.C(N1CCCC(CC(C2C=CC(F)=CC=2)=O)C1)#N.Cl.[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44]>C(OCC)C.O.C(O)(=O)C.C1C=CC=CC=1>[C:40]([OH:47])(=[O:46])/[CH:41]=[CH:42]\[C:43]([OH:45])=[O:44].[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:12](=[O:13])[CH2:11][CH:7]2[CH2:8][CH2:9][CH2:10][NH:5][CH2:6]2)=[CH:19][CH:18]=1

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 10476Cyanogen BromideHCID 444266Maleic AcidHCID 123645001-Methyl-3-(4-fluorophenacyl)piperidineHCID 215303571-Cyano-3-(4-fluorophenacyl)piperidine

생성물 1

HCID 1317103173-(4-Fluorophenacyl)piperidine, maleate salt

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 241Benzene용매HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

The procedure of Example 19 was repeated to give 19 g of crude 1-cyano-3-(4-fluorophenacyl)piperidine, except that 5.4 g of cyanogen bromide, 10.0 g of 1-methyl-3-(4-fluorophenacyl)piperidine (Example 3), and 110 ml of benzene were employed and the addition was carried out at ambient temperature over a 45-minute period. The crude cyanopiperidine was hydrolyzed as described in Example 21, using as the hydrolysis mixture a solution consisting of 80 ml of glacial acetic acid, 40 ml of water, and 20 ml of concentrated hydrochloric acid; hydrolysis time was increased to 19 hours. The final residue was taken up in diethyl ether and combined with a solution of 2.6 g of maleic acid in 200 ml of diethyl ether. An oil separated which crystallized upon standing. The solid, 5.5 g, was recrystallized 3 times from acetone/diethyl ether to give 3-(4-fluorophenacyl)piperidine, maleate salt, mp 131°-132°. The following elemental analysis was obtained:

후처리

  1. additionthe addition
  2. waitwas carried out at ambient temperature over a 45-minute period
  3. customhydrolysis time
  4. temperaturewas increased to 19 hours
  5. customAn oil separated which
  6. customcrystallized
  7. customThe solid, 5.5 g, was recrystallized 3 times from acetone/diethyl ether

출처 및 근거

ORD 기록
ord-577330e8d09b41e8bc02f01fccec1fe8
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03962257

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