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

HRID 1768571

反応式

HRID 1768571 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e842eb7785cb422790b5f8f18349cf51
出典データセット
uspto-grants-1995_01
特許番号
US05378714

関連ノート

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