Sodium borohydride → HCID 54428684, compound

HRID 372422Notes

Reaction equation

HRID 372422 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[O:16][C:15]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:14]=3[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH:12]2[C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[O:16][C:15]3[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:14]=3[CH2:13]2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54533726HCID 54533726, compound

Product 1

HCID 54428684HCID 54428684, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

48.6 G. of 4-[2,8-dimethyl-dibenz[b,f]oxepin-10-yl]-1-piperazinecarboxylic acid ethyl ester are dissolved in 750 ml. of glacial acetic acid. 18.9 G. of sodium borohydride are added in small portions within 20 minutes with stirring and cooling in such a manner that the temperature does not exceed 25° C. The mixture is stirred for an additional 30 minutes at 25° C. and then the glacial acetic acid is removed by distillation in vacuo. The residue is partitioned between chloroform and aqueous sodium hydroxide solution. The organic phase is separated and washed with water. The aqueous phases are extracted two additional times with chloroform. The combined chloroform extracts are dried over sodium sulfate, evaporated in vacuo, and there is obtained crude 4-[10,11-dihydro-2,8-dimethyldibenz[b,f]oxepin-10-yl]-1-piperazinecarboxylic acid ethyl ester as an oil.

Workup

  1. temperaturecooling in such a manner that the temperature
  2. customdoes not exceed 25° C
  3. stirringThe mixture is stirred for an additional 30 minutes at 25° C.
  4. customthe glacial acetic acid is removed by distillation in vacuo
  5. customThe residue is partitioned between chloroform and aqueous sodium hydroxide solution
  6. customThe organic phase is separated
  7. washwashed with water
  8. extractionThe aqueous phases are extracted two additional times with chloroform
  9. dry with materialThe combined chloroform extracts are dried over sodium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-76d8b78b62ff406a9412a6876ca24b1b
Source dataset
uspto-grants-1978_05
Patent number
US04091023

Reaction notes

Loading…