Ammonium Chloride → HCID 12019532, compound

HRID 2054733Notes

Reaction equation

HRID 2054733 reaction equation
[CH:1]1([C:7]2[CH:21]=[CH:20][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[C:15]#[N:16])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C(OCC)C.C1COCC1>[CH:1]1([C:7]2[CH:21]=[CH:20][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[CH2:15][NH2:16])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 12019531HCID 12019531, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12019532HCID 12019532, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., a solution of 600 mg (2.16 mmol) of 3-(4-cyclohexylphenoxy)benzonitrile from Ex. I in 6 ml of anhydrous diethyl ether is added dropwise to 4.32 ml (4.32 mmol) of a 1-molar solution of LiAlH4 in THF. Over a period of 4 h, the reaction mixture is warmed to room temperature, and 10 ml of a sat. solution of NH4Cl are then added carefully, the mixture is diluted with ether and the organic phase is removed. The organic phase is washed successively with water and a sat. solution of NaCl, dried over MgSO4 and, after filtration, freed from the solvent. This gives 573 mg (1.81 mmol, purity 88.82%, 84% yield) of 3-(4-cyclohexylphenoxy)-benzylamine.

Workup

  1. customAt 0° C.
  2. customthe organic phase is removed
  3. washThe organic phase is washed successively with water
  4. dry with materiala sat. solution of NaCl, dried over MgSO4
  5. filtrationafter filtration

Sources & evidence

ORD record
ord-ce02877fa20f462ba4d1528684393928
Source dataset
uspto-grants-2008_02
Patent number
US07329777B2

Reaction notes

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