Dicyclohexylcarbodiimide → N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide

HRID 1981362

반응식

HRID 1981362 반응식
[C:1]([OH:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N+:4]([O-:8])[CH:3]=1.[CH:11]1(N=C=NC2CCCCC2)CCCCC1.C[CH:27]([N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[C:28]1[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=1)[O:31][CH2:32][CH2:33][CH2:34][NH2:35]>CN(C)C1C=CN=CC=1.C(#N)C>[CH3:11][CH:43]1[CH2:42][CH2:41][CH2:40][N:39]([CH2:27][C:28]2[CH:29]=[C:30]([CH:36]=[CH:37][CH:38]=2)[O:31][CH2:32][CH2:33][CH2:34][NH:35][C:1]([C:2]2[CH:3]=[N+:4]([O-:8])[CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:44]1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 16976Oxiniacic AcidHCID 205671913-[3-(Methylpiperidinomethyl)phenoxy]propylamine

생성물 1

HCID 6917813N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매2회

실험 절차

To a solution of 5 g of 4-dimethylaminopyridine in 80 ml of acetonitrile there is added 5.6 g of nicotinic acid 1-oxide. The mixture is stirred 10 minutes at room temperature and then added with 9.2 g of dicyclohexylcarbodiimide. After standing 5 minutes at room temperature, there are added 10 g of 3-[3-(methylpiperidinomethyl)phenoxy]propylamine dissolved in 20 ml of acetonitrile. A weakly exothermic reaction (from 20° to 25° C.) and a dissolution which within 5 minutes is almost completed, are observed. Then the mixture is stirred 4 hours at 40° C. and the dicyclohexylurea which forms is filtered and washed with acetonitrile. After evaporation to dryness under reduced pressure, the residue is purified by chromatography on silica as described in Example 7. Thus, the N-[3-[3-(3-methylpiperidinomethyl)phenoxy]propyl]-3-pyridinecarboxamide 1-oxide is obtained, identical to the product of Example 8; m.p. 108°-110° C.

후처리

  1. waitAfter standing 5 minutes at room temperature
  2. customA weakly exothermic reaction (from 20° to 25° C.)
  3. dissolutiona dissolution which within 5 minutes
  4. stirringThen the mixture is stirred 4 hours at 40° C.
  5. filtrationthe dicyclohexylurea which forms is filtered
  6. washwashed with acetonitrile
  7. customAfter evaporation to dryness under reduced pressure
  8. customthe residue is purified by chromatography on silica

출처 및 근거

ORD 기록
ord-058b48b2507348a19f6b9a22f71dfac1
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04514408

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