Sodium Hydroxide → HCID 70625700, compound

HRID 1112205Notes

Reaction equation

HRID 1112205 reaction equation
C(O[C:4]([N:6]1[CH2:20][CH2:19][CH:18]2[N:9]([CH:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH2:17]2)[CH2:8][CH2:7]1)=O)C.[H-].COCCO[Al+2].[Na+].[Na+].[H-].[H-].[H-].[OH-].[Na+]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH3:4][N:6]1[CH2:20][CH2:19][CH:18]2[N:9]([CH:10]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH2:17]2)[CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 70624874HCID 70624874, compoundHCID 86736071HCID 86736071, compound

Product 1

HCID 70625700HCID 70625700, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 6.8 g of (7RS,12aRS)-1,2,3,4,5,7,12,12a-octahydro-7-phenyl-1,4-diazepino[1,7-b]isoquinoline-3-carboxylic acid ethyl ester in toluene was added dropwise slowly into a stirred and boiling mixture of 200 ml of toluene and 21.6 ml of 70% disodium (2-methoxyethoxy)aluminium hydride in benzene. The reaction mixture was refluxed for a further 30 minutes, and cooled to 0°. The complex and remaining reducing agent was decomposed by the slow dropwise addition of 60 ml of a 20% sodium hydroxide solution. The organic phase was separated off, washed with 100 ml of a 20% sodium hydroxide solution, then washed three times with water, then dried with magnesium sulphate, and finally concentrated to dryness to give the title compound (M.P. of maleate from methanol/ether 184°-186°).

Workup

  1. temperatureThe reaction mixture was refluxed for a further 30 minutes
  2. temperaturecooled to 0°
  3. customThe organic phase was separated off
  4. washwashed with 100 ml of a 20% sodium hydroxide solution
  5. washwashed three times with water
  6. dry with materialdried with magnesium sulphate
  7. concentrationfinally concentrated to dryness

Sources & evidence

ORD record
ord-0b43de09f6fe4c8d8fc03cfc8227845b
Source dataset
uspto-grants-1978_10
Patent number
US04120965

Reaction notes

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