Ammonium Chloride → 1-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(4-methoxyphenyl)piperidine hydrochloride

HRID 1649371Notes

Reaction equation

HRID 1649371 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]3)=[N:7][O:8][C:4]=2[CH:3]=1.C([Mg]Br)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.[Cl-:32].[NH4+]>O1CCCC1.CCOCC>[ClH:32].[F:1][C:2]1[CH:20]=[CH:19][C:5]2[C:6]([CH2:9][CH2:10][CH2:11][N:12]3[CH2:13][CH2:14][C:15]([OH:18])([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:16][CH2:17]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 132078191-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidoneHCID 178418276HCID 178418276, compound

Product 1

HCID 132078271-[3-(6-Fluoro-1,2-benzisoxazol-3-yl)propyl]-4-hydroxy-4-(4-methoxyphenyl)piperidine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.3 g of 1-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-4-piperidone in 35 ml of tetrahydrofuran was slowly added to a solution of 49 ml of p-anisylmagnesium bromide (1.4 M in tetrahydrofuran). After the addition was complete, the reaction mixture was stirred at ambient temperature for one hr, diluted with ether, poured into 400 ml of saturated ammonium chloride solution and extracted with ether. The organic extracts were washed with water (2×), saturated sodium chloride solution and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was converted to 8.5 g (89%) of product, mp 100°-105° C., by treatment with ethereal hydrogen chloride. An analytical sample was obtained by recrystallization from ethyl acetate/methanol and had mp 181°-182° C. (dec).

Workup

  1. additionAfter the addition
  2. extractionextracted with ether
  3. washThe organic extracts were washed with water (2×), saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAn analytical sample was obtained by recrystallization from ethyl acetate/methanol

Sources & evidence

ORD record
ord-4251451962354161b5449acb9a9fa842
Source dataset
uspto-grants-1983_11
Patent number
US04416887

Reaction notes

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