Sodium Hydroxide → 189153-13-7

HRID 1600686Notes

Reaction equation

HRID 1600686 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].O=[C:12]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH2:20])[CH2:16][CH2:15]1.[OH-].[Na+]>C1COCC1.CCOCC.O>[C:27]1([N:24]2[CH2:23][CH2:22][N:21]([CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]3)[CH2:26][CH2:25]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 178511526HCID 178511526, compound

Product 1

HCID 10684726189153-13-7

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of LiAlH4 (3.32 g, 0.0875 mol) in dry THF (125 mL) at 0° was treated with a solution of AlCl3 (40 g, 0.03 mol) in dry Et2O (125 mL) and stirred for 30 minutes. Over a 10-minute period, a solution of trans-{4-[2-oxo-2-(4-phenyl-piperazin-1-yl)-ethyl]-cyclohexyl}-amine (10.54 g, 0.035 mol) in THF (150 mL) was added, and the reaction mixture was allowed to warm to room temperature. After 20 hours, the reaction mixture was cooled in ice-water and treated with THF (50 mL) containing H2O (3 mL), then with 50% NaOH (3 mL) and H2O (6 mL). The inorganic material was filtered off through a Celite pad, and the solids were washed thoroughly with THF. The combined filtrates were evaporated to dryness, and the residue was taken up in CH2Cl2, dried (Na2SO4), and concentrated to yield trans-N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]-cyclohexylamine as a white solid, 9.64 g (96%), which was used without further purification; mp 65-70° C.

Workup

  1. waitOver a 10-minute period
  2. waitAfter 20 hours
  3. filtrationThe inorganic material was filtered off through a Celite pad
  4. washthe solids were washed thoroughly with THF
  5. customThe combined filtrates were evaporated to dryness
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8945d888ff904db2ab32b28e2fd4acf1
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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