Water → 3-[1-(1-Hydroxyhex-6-yl]-4-piperidinyl]-6-fluoro-1,2-benzisoxazole

HRID 1768571

반응식

HRID 1768571 반응식
Cl.[F:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Li+].[Li+].Cl[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][OH:31].O>CN(C=O)C>[OH:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[C:6]3[CH:16]=[CH:17][C:3]([F:2])=[CH:4][C:5]=3[O:9][N:8]=2)[CH2:15][CH2:14]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11125Lithium CarbonateHCID 748286-Chloro-1-hexanolHCID 11334359R-56109 hydrochloride

생성물 1

HCID 189489303-[1-(1-Hydroxyhex-6-yl]-4-piperidinyl]-6-fluoro-1,2-benzisoxazole수율 25.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (1g, 3.9 mmol), lithium carbonate (865 mg, 1.7 mmol) and 6-chloro-1-hexanol (534 mg, 3.9 mmol) in 5 ml dry DMF was heated at 100° C. for 48 h. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with water, brine, dried with sodium sulphate and concentrated in vacuo. The crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1, v/v). Concentration of the appropriate fractions afforded 310 mg (25.6%) of 3-[1-(1-hydroxyhex-6-yl)-4-piperidinyl]-6-fluoro-1, 2-benzisoxazole as an oil.

후처리

  1. extractionthe aqueous mixture was extracted with ethyl acetate
  2. washThe ethyl acetate phase was washed with water, brine
  3. dry with materialdried with sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1

출처 및 근거

ORD 기록
ord-e842eb7785cb422790b5f8f18349cf51
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378714

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