Pyrrolidine → tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate

HRID 1005653

반응식

HRID 1005653 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=2[N+:21]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24]OC(OC)N(C)C.N1CCCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:15]=2[NH:21][CH:24]=[CH:20]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 601087754-(3-Methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 21070951tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate수율 26.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-(3-methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, 31 mmol), N,N-dimethylformamide dimethyl acetal (13.2 mL, 100 mmol) and pyrrolidine (4 mL, 50 mmol) in 45 mL of DMF was heated under reflux for 20 h. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate was dried and evaporated. The residue was hydrogenated in 200 mL of THF containing 2.5 g of 10% Pd-C at 50 psi for 6 h. The mixture was filtered, concentrated in vacuo, and partitioned between ethyl acetate and aqueous HCl. The ethyl acetate was washed with brine, dried and evaporated. Silica gel chromatography (10% ethyl acetate-hexane) afforded 2.5 g of 4-(1H-Indol-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (19) as a white solid, m.p. 150-151° C.

후처리

  1. temperatureunder reflux for 20 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate was dried
  5. customevaporated
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated in vacuo
  8. custompartitioned between ethyl acetate and aqueous HCl
  9. washThe ethyl acetate was washed with brine
  10. customdried
  11. customevaporated

출처 및 근거

ORD 기록
ord-159b9b19f9c24f1eb3a2e5b4c77702d4
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787535B2

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