Sodium hydride → 4-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1373638

반응식

HRID 1373638 반응식
[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([NH2:11])[C:4]=2[O:3]1.[C:13]([O:17][C:18](=[O:26])[N:19]([CH2:23][CH2:24]Cl)[CH2:20][CH2:21]Cl)([CH3:16])([CH3:15])[CH3:14].[H-].[Na+]>CN(C=O)C>[C:13]([O:17][C:18]([N:19]1[CH2:23][CH2:24][N:11]([C:10]2[C:4]3[O:3][C:2]([F:1])([F:12])[O:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)[CH2:21][CH2:20]1)=[O:26])([CH3:16])([CH3:15])[CH3:14]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27368912,2-Difluoro-1,3-dioxaindan-4-amineHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

생성물 1

HCID 694174874-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester수율 22.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

An intermediate compound, 1-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-piperazine, was produced as follows: To the mixture of 2,2-difluoro-benzo[1,3]dioxol-4-ylamine (27 g, 0.156 mol) and bis-(2-chloro-ethyl)-carbamic acid tert-butyl ester (75.5 g, 0.31 mol) in DMF (500 mL) was added NaH (15.6 g, 60% oil dispersion, 0.39 mol) at 0° C. and the resulting mixture was stirred at room temperature for 24 h until LCMS indicated the starting material disappeared. The reaction was quenched with aq. NH4Cl, extracted with EtOAc, washed with brine, dried and concentrated. The residue was purified by flash chromatography (Et3N:EtOAc:heptane/1:10:100) to afford 4-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (12.0 g, 22%) as colorless crystals.

후처리

  1. customThe reaction was quenched with aq. NH4Cl
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (Et3N:EtOAc:heptane/1:10:100)

출처 및 근거

ORD 기록
ord-8e099b4593f5486a974eba2aa0e3f8f2
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160888B2

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