1-Hydroxybenzotriazole → 4-[4-(phenylmethyl)-1-piperazinyl]-N-[(tetrahydro-2H-pyran-2-yl)oxy]-benzamide

HRID 1160153노트

반응식

HRID 1160153 반응식
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[O:29][NH2:30].ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][N:11]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([NH:30][O:29][CH:24]4[CH2:25][CH2:26][CH2:27][CH2:28][O:23]4)=[O:19])=[CH:21][CH:22]=3)[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 757711-HydroxybenzotriazoleHCID 47417244-(4-benzylpiperazin-1-yl)benzoic AcidHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

생성물 1

HCID 865980264-[4-(phenylmethyl)-1-piperazinyl]-N-[(tetrahydro-2H-pyran-2-yl)oxy]-benzamide수율 95.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-[4-(phenylmethyl)-1-piperazinyl]-benzoic acid (0.0145 mol), O-(tetrahydro-2H-pyran-2-yl)-hydroxylamine (0.029 mol), N,N-methanetetrayl-biscyclohexanamine (0.0145 mol) and 1-hydroxy-1H-benzotriazole (0.021 mol) in DCM p.a. (200 ml) was stirred at room temperature over the weekend. The reaction mixture was washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from EtOAc, filtered off and dried, yielding 3.5 g and another crop: 2.0 g total yielding 5.5 g (95%) of 4-[4-(phenylmethyl)-1-piperazinyl]-N-[(tetrahydro-2H-pyran-2-yl)oxy]-benzamide (interm. 8).

후처리

  1. washThe reaction mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue was crystallized from EtOAc
  6. filtrationfiltered off
  7. customdried
  8. customyielding 3.5 g

출처 및 근거

ORD 기록
ord-30cdc1a93174478f991ee213a941f18a
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816363B2

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