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Potassium Iodide → 4'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochloride

HRID 1580276
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HRID 1580276 반응식
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]21[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:26][CH2:27][CH2:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)=[O:31]>CN(C)C=O>[ClH:26].[F:38][C:35]1[CH:34]=[CH:33][C:32]([C:30](=[O:31])[CH2:29][CH2:28][CH2:27][NH:17][CH:14]2[CH2:13][CH2:12][C:3]3([CH2:4][CH2:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:2]3)[CH2:16][CH2:15]2)=[CH:37][CH:36]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 122512743',4'-Dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride

생성물 1

HCID 122512764'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochloride수율 39%

시약·촉매·용매

1
HCID 6228Dimethylformamide용매

실험 절차

The free base from 1.65 g. (0.0066 M) of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride [I(c)] (prepared in Example 10C), 1.34 g. of potassium iodide, 2.06 g. of potassium carbonate and 1.9 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone in 35 ml. of dimethylformamide are heated in an oil bath at about 90° C. for about 18 hours. The solvent is removed under vacuum and the residue that remains in dissolved in benzene and water. The organic layer is washed with water and brine and evaporated to dryness. A mixture of the residue and 10 ml. of 2.5 N hydrochloric acid in 20 ml. of methanol is stirred at room temperature for about 4 hours. The methanol is then removed under vacuum and the solid collected on a filter. This material is recrystallized twice from methylene chloride: ethyl acetate to give 1.07 g. (39% yield) of 4'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochloride [I(c), having a melting point of 182° to 184° C.

후처리

  1. customThe solvent is removed under vacuum
  2. dissolutionin dissolved in benzene
  3. washThe organic layer is washed with water and brine
  4. customevaporated to dryness
  5. additionA mixture of the residue and 10 ml
  6. customThe methanol is then removed under vacuum
  7. customthe solid collected on a filter
  8. customThis material is recrystallized twice from methylene chloride
  9. customethyl acetate to give 1.07 g

출처 및 근거

ORD 기록
ord-bb4d4835311a40d182baef3170f3e544
출처 데이터셋
uspto-grants-1976_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03932425

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