Laurolactam → n-(cis-2-Phenyl-cyclopentyl) azacyclotridecan-2-imine-hydrochloride

HRID 262004

반응식

HRID 262004 반응식
[C:1]1(=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.P(Cl)(Cl)([Cl:17])=O.Cl.[C:21]1([C@H:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[NH2:32])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1C=CC=CC=1>[ClH:17].[C:21]1([C@H:27]2[CH2:31][CH2:30][CH2:29][C@H:28]2[N:32]=[C:1]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 13690LaurolactamHCID 24813Phosphorus oxychlorideHCID 70051154rac-(1R,2R)-2-phenylcyclopentan-1-amine hydrochloride

생성물 1

HCID 136349517n-(cis-2-Phenyl-cyclopentyl) azacyclotridecan-2-imine-hydrochloride

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To 21.7 g of 2-azacyclotridecanone in 200 ml of dry benzene was added dropwise 15.3 g of phosphorus oxychloride. The mixture was stirred at room temperature for 4 hours after which 19.8 g of cis-2-phenylcyclopentylamine hydrochloride was added. The reaction mixture was stirred at room temperature for 2 hours and refluxed for 24 hours. The resulting homogeneous solution was washed with 2 N NaOH, 2 N HCl and saturated NaCl solution, dried over sodium sulfate and the solvent evaporated. The resulting oily product crystallized from acetone and was recrystallized from methanol-acetone to give the desired product, M.P. 156°-159° C.

후처리

  1. additionwas added
  2. temperaturerefluxed for 24 hours
  3. washThe resulting homogeneous solution was washed with 2 N NaOH, 2 N HCl and saturated NaCl solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvent evaporated
  6. customThe resulting oily product crystallized from acetone
  7. customwas recrystallized from methanol-acetone

출처 및 근거

ORD 기록
ord-762009176f41401383768f2958878274
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153235

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