Ammonia → 3-p-biphenylyl-butylamine. Hydrochloride

HRID 2420587Notes

Reaction equation

HRID 2420587 reaction equation
I.C(O)(=O)C.C(O[C:9](=O)[CH2:10][C:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(O)[CH3:12])C.O=S(Cl)[Cl:29].[Cl-].[NH3:32].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[ClH:29].[C:15]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]([CH3:12])[CH2:10][CH2:9][NH2:32]

Participants

10

Reactant 7

HCID 222AmmoniaHCID 312ChlorideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 18398580Eisessig-JodwasserstoffHCID 21226445Aluminium lithium hydrideHCID 705973773-p-Biphenylyl-3-hydroxy-butyric acid ethyl ester

Product 1

HCID 705974403-p-biphenylyl-butylamine. Hydrochloride

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 23.9 g of 3-p-biphenylyl-butyramide [m.p. 156°- 158°' obtainable by Friedel-Crafts acetylation of biphenyl to give 4-acetylbiphenyl (m.p. 118°- 120°), reaction with bromoacetic acid ethyl ester/zinc to give 3-p-biphenylyl-3-hydroxy-butyric acid ethyl ester (m.p. 55°- 56°), treatment with HI/acetic acid, reaction of the resulting 3-p-biphenylyl-butyric acid (m.p. 118°- 12-°) with SOCl2 to give the chloride, and reaction with ammonia] in 500 ml of THF is added dropwise, while stirring, to a suspension of 7.6 g of LiAlH4 in 250 ml of absolute THF, the mixture is boiled for 16 hours, ethyl acetate is added, with cooling, followed by 32% sodium hydroxide solution and the mixture is worked up in the customary manner to give 3-p-biphenylyl-butylamine. Hydrochloride, m.p. 226°-228°.

Workup

  1. customto give
  2. additionis added dropwise
  3. temperaturewith cooling

Sources & evidence

ORD record
ord-5bcc1028357e424280765a2b3d77a06f
Source dataset
uspto-grants-1978_08
Patent number
US04110447

Reaction notes

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