Dimethylformamide → 6-Phenylazepan-2-one

HRID 569752노트

반응식

HRID 569752 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.CN1CCOCC1.CN(C)C=O.Cl.[NH2:31][CH2:32][CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:34][CH2:35][CH2:36][C:37](O)=[O:38]>C(OCC)(=O)C.O>[C:40]1([CH:33]2[CH2:32][NH:31][C:37](=[O:38])[CH2:36][CH2:35][CH2:34]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 199401P,P-Diphenylphosphinic azideHCID 679105716-Amino-5-phenylhexanoic acid hydrochloride

생성물 1

HCID 127649286-Phenylazepan-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

27.6 ml of diphenylphosphoryl azide and then 37.5 ml of N-methylmorpholine were added to 260 ml of dimethylformamide containing 26.0 g of 6-amino-5-phenylhexanoic acid hydrochloride [prepared as described in step (c) above] in an ice-bath. The reaction mixture was stirred for 3.5 hours at room temperature, and then dissolved in 0.5 liter of ethyl acetate and 0.5 liter of water. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography using a 2:1 by volume mixture of ethyl acetate and methylene chloride as eluent, to give 4.0 g of the title compound as crystals, melting at 153.5°-154.5° C. (with decomposition).

후처리

  1. customThe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. additionby volume mixture of ethyl acetate and methylene chloride as eluent

출처 및 근거

ORD 기록
ord-1c7deeb93ff3471b9d9fd5f051853c33
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04734410

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