Hydrochloric Acid → HCID 131711218, compound

HRID 2420588Notes

Reaction equation

HRID 2420588 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:19])[CH2:15][C:16]([NH2:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.B#B.Cl.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:19])[CH2:15][CH2:16][NH2:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6328200DiboronHCID 20302328HCID 20302328, compound

Product 1

HCID 131711218HCID 131711218, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 27.5 g of 3-(4'-chloro-4-biphenylyl)butyramide [m.p. 185° - 187°; obtainable from p-chlorobiphenyl via 4-acetyl-4'-chlorobiphenyl (m.p. 100° - 103°), 3-(4'-chloro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester (m.p. 72°-74°) and 3-(4'-chloro-4-biphenylyl)-butyric acid (m.p. 154°-156°)] in 300 ml of THF is added dropwise, while stirring, to a solution of 4.6 g of diborane in 50 ml of THF, and the mixture is boiled for two hours, cooled and treated with 25% hydrochloric acid. It is then poured into water and worked up with sodium hydroxide solution and ethyl acetate to give 3-(4'-chloro-4-biphenylyl)-butylamine. Hydrochloride, m.p. 256°-259°.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-3734c685c9694cd6b8e56753b523b018
Source dataset
uspto-grants-1978_08
Patent number
US04110447

Reaction notes

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