Diethyl Ether → HCID 12338798, compound

HRID 1578484Notes

Reaction equation

HRID 1578484 reaction equation
[Br:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]([N:13]2[CH2:18][CH2:17][N:16]([N:19]=O)[CH2:15][CH2:14]2)[C:5]2[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=2[CH:3]=1.CCOCC.[Li+].[AlH4-].[OH-].[Na+]>O.O1CCCC1>[Br:1][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]([N:13]2[CH2:14][CH2:15][N:16]([NH2:19])[CH2:17][CH2:18]2)[C:5]2[CH:21]=[CH:22][CH:23]=[CH:24][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 12338797HCID 12338797, compound

Product 1

HCID 12338798HCID 12338798, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 20 parts of 1-(10-bromo-5H-dibenzo[a,d]cyclohepten-5-yl)-4-nitrosopiperazine in 1400 parts of anhydrous ether is slowly added 7 parts of lithium tetrahydroaluminate(1-). The resultant mixture is stirred at room temperatures for 5 hours, then cooled to around 5° and maintained thereat while a solution of 14 parts of water in 25 parts of tetrahydrofuran, 18 parts of aqueous 25% sodium hydroxide, and 14 parts of water are consecutively introduced. Insoluble solids are removed by filtration and washed with tetrahydrofuran. The washings and filtrate are combined, dried over anhydrous magnesium sulfate, and stripped of solvent by vacuum distillation. The residual yellow solid is crystallized from a mixture of tetrahydrofuran and hexane to give 1-(10-bromo-5H-dibenzo[a,d]cyclohepten-5-yl)-4-piperazineamine as colorless crystals melting at 187.5°-190.5°.

Workup

  1. temperaturecooled to around 5°
  2. temperaturemaintained
  3. customInsoluble solids are removed by filtration
  4. washwashed with tetrahydrofuran
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationstripped of solvent by vacuum distillation
  7. customThe residual yellow solid is crystallized from a mixture of tetrahydrofuran and hexane

Sources & evidence

ORD record
ord-387ad9fa5e344519908c37d06bbe917d
Source dataset
uspto-grants-1976_02
Patent number
US03937701

Reaction notes

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