Sodium amide → Indan-2-yl-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]phenylamine

HRID 2167086노트

반응식

HRID 2167086 반응식
[NH2-].[Na+].[CH2:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.Cl[CH2:21][CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH3:28]>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][CH:4]1[N:12]([CH2:21][CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH3:28])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 24533Sodium amideHCID 118068N-phenylindan-2-amineHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)

생성물 1

HCID 68180914Indan-2-yl-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]phenylamine

시약·촉매·용매 2

HCID 1140Toluene용매3회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred suspension of sodamide (256 mg, 6.58 mmol) in toluene (10 mL) was added a solution of indan-2-yl-phenyl-amine (7; 1.0 g, 4.78 mmol) in toluene (5 mL) at 0° C. The reaction mixture was stirred at rt for 3 hours. A solution of 2-(2-chloroethyl)-1-methyl-pyrrolidine hydrochloride (18; 0.808 g, 4.39 mmol) in toluene (5 mL) was added to the reaction mixture and the resulting mixture was refluxed for 16 hours. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography on neutral alumina eluting with 0.8% methanol-DCM to provide compound 19.

후처리

  1. temperaturethe resulting mixture was refluxed for 16 hours
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by column chromatography on neutral alumina eluting with 0.8% methanol-DCM

출처 및 근거

ORD 기록
ord-cf7c86112c224565831ee5cb730c655b
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09044482B2

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