Acetone → HCID 20302326, compound

HRID 2420600Notes

Reaction equation

HRID 2420600 reaction equation
Cl.Br[C:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)([CH3:7])[CH2:4][CH2:5][NH2:6].CC(C)=[O:23]>O.S(=O)(=O)(O)O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:3]([OH:23])([CH3:7])[CH2:4][CH2:5][NH2:6])=[CH:9][CH:10]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 20302722HCID 20302722, compound

Product 1

HCID 20302326HCID 20302326, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

3.59 g of 3-bromo-3-(4'-fluoro-4-biphenylyl)butylamine hydrochloride [obtainable by reacting 3-hydroxy-3-(4'-fluoro-4-biphenylyl)-butyramide with PBr3 to give 3-bromo-3-(4'-fluoro-4-biphenylyl)-butyramide and reduction with LiAlH4 ] are dissolved in a mixture of 15 ml of acetone and 15 ml of water, 1 drop of sulfuric acid is added, and the mixture is warmed to 45° for 4 hours and worked up in the customary manner to give 3-(4'-fluoro-4-biphenylyl)-3-hydroxybutylamine, m.p. 144° - 146°. A little 3-(4'-fluoro-4-biphenylyl)-2-butenylamine, which can be removed by chromatography (over SiO2), is formed as a by-product.

Workup

  1. additionis added
  2. temperaturethe mixture is warmed to 45° for 4 hours

Sources & evidence

ORD record
ord-cca6c2d519d6488297535c39b6ca584d
Source dataset
uspto-grants-1978_08
Patent number
US04110447

Reaction notes

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