Sodium Hydroxide → HCID 178420461, compound

HRID 893329Notes

Reaction equation

HRID 893329 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C@H:20]2[CH2:25][CH2:24][C@H:23]([CH2:26][C:27]([N:29]3[CH2:34][CH2:33][N:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:31][CH2:30]3)=O)[CH2:22][CH2:21]2)=[CH:12]1.[OH-].[Na+]>O1CCCC1.O>[N:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[N:32]1[CH2:33][CH2:34][N:29]([CH2:27][CH2:26][C@H:23]2[CH2:24][CH2:25][C@H:20]([C:13]3[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[NH:11][CH:12]=3)[CH2:21][CH2:22]2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 178520735HCID 178520735, compound

Product 1

HCID 178420461HCID 178420461, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A slurry of lithium aluminum hydride (0.472 g, 12.4 mmol) in 20 mL of tetrahydrofuran at 0° C. is treated with aluminum chloride (0.553 g, 4.15 mmol) and the mixture is stirred for 20 minutes. A slurry of trans 1-(2-{4-[1H-3-indolyl]-cyclohexyl}acetyl)-4-(2-pyridinyl)piperazine (1.67 g, 4.15 mmol) in 20 mL of tetrahydrofuran is added and the reaction is stirred at ambient temperature for 18 hours. Water (1 mL) and 10% sodium hydroxide solution (2 mL) is added the mixture is stirred for 2 hours, then filtered through celite and the volatiles are removed under reduced pressure. The resulting oil is triturated with diethyl ether to give the product as a white solid (1.57 g); mp 147°-148° C.

Workup

  1. stirringthe reaction is stirred at ambient temperature for 18 hours
  2. stirringis stirred for 2 hours
  3. filtrationfiltered through celite
  4. customthe volatiles are removed under reduced pressure
  5. customThe resulting oil is triturated with diethyl ether

Sources & evidence

ORD record
ord-4d62875a4434487296307b51e63afe1a
Source dataset
uspto-grants-1992_06
Patent number
US05124332

Reaction notes

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