Sulfuric Acid → HCID 20302326, compound

HRID 1733044Notes

Reaction equation

HRID 1733044 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5].[CH3:19]I.[Mg].S(=O)(=O)(O)O>C1COCC1.CCOCC.O>[F:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[CH:11][C:6]([C:4]([OH:5])([CH3:19])[CH2:3][CH2:2][NH2:1])=[CH:7][CH:8]=2)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 20302101HCID 20302101, compound

Product 1

HCID 20302326HCID 20302326, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 24.4 g of 1-amino-3-(4'-fluoro-4-biphenylyl)-propan-3-one [obtainable by reacting 1-chloro-3-(4'-fluoro-4-biphenylyl)-propan-3-one with potassium phthalimide and subsequent hydrolysis] in 200 ml of THF is added dropwise, while stirring, at 20° to a Grignard solution prepared from 30 g of CH3I and 5 g of magnesium in 1000 ml of ether. The mixture is stirred for a further 4 hours, the resulting alcoholate is decomposed by means of water and dilute sulfuric acid, and the mixture is worked up in the customary manner to give 3-(4'-fluoro-4-biphenylyl)-3-hydroxybutylamine, m.p. 144°-146°.

Workup

  1. stirringThe mixture is stirred for a further 4 hours

Sources & evidence

ORD record
ord-25a498c8d60b494fb5f27172d6e5d924
Source dataset
uspto-grants-1980_12
Patent number
US04239759

Reaction notes

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