Ammonia → 3-(4'-Fluoro-4-biphenylyl)butylamine, hydrochloride

HRID 2420599Notes

Reaction equation

HRID 2420599 reaction equation
O=S(Cl)[Cl:3].N.BrBr.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:27])[CH2:22][CH2:23][N:24]=C=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>O1CCOCC1.[OH-].[K+].CCOCC.O.CO>[ClH:3].[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:27])[CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

10

Reactant 4

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 24408BromineHCID 540086763-(4'-Fluoro-4-biphenylyl)-butyl-isocyanate

Product 1

HCID 203027163-(4'-Fluoro-4-biphenylyl)butylamine, hydrochloride

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×HCID 14797Potassium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 27.1 g of 4-(4'-fluoro-4-biphenylyl)-pentanoic acid amide [obtainable by reacting 4-fluorobiphenyl with succinic anhydride/AlCl3 to give 4-(4'-fluoro-4-biphenylyl)-4-oxobutanoic acid, reaction with CH3MgI to give 4-(4'-fluoro-4-biphenylyl)-4-hydroxy-pentanoic acid, dehydroxylation with HI/acetic acid to give 4-(4'-fluoro-4-biphenylyl)-pentanoic acid, conversion into the chloride employing SOCl2 and reaction with NH3 ] in 150 ml of dioxane is added dropwise at 0° to a solution of 24 g of bromine in 120 ml of 20% potassium hydroxide solution. The mixture is stirred for a further 1 hour, taken up in ether, the phases are separated and the organic phase is dried over sodium sulfate and evaporated. The crude product obtained is boiled for 20 hours with 60 g of KOH, 250 ml of methanol and 65 ml of water, in the course of which 3-(4' -fluoro-4-biphenylyl)-butyl-isocyanate, which is not isolated, is formed. After cooling, the mixture is worked up using water and ether to give 3-(4'-fluoro-4-biphenylyl)-butylamine, hydrochloride; m.p. 222°-224°.

Workup

  1. customthe phases are separated
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customevaporated
  4. customThe crude product obtained
  5. customis not isolated
  6. customis formed
  7. temperatureAfter cooling

Sources & evidence

ORD record
ord-4debed1c123140cab1e87556ccee3cbd
Source dataset
uspto-grants-1978_08
Patent number
US04110447

Reaction notes

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