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

HRID 1704261노트

반응식

HRID 1704261 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 2N NaOH, 2N 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 2N NaOH, 2N 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-d9ea297fa37940b8bf61aa432df2cad9
출처 데이터셋
uspto-grants-1978_11
특허 번호
US04126621

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