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Hydrochloric Acid → HCID 22903535, compound

HRID 1440273
Notes
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Reaction equation

HRID 1440273 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:37])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:36])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][CH2:30][C:31](OCC)=[O:32])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:38]=1.CO[BH-](OC)OC.[Na+].Cl>COCCOC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:37])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:36])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:38]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3084262Sodium hydrotrimethoxyborate(1-)HCID 22903504HCID 22903504, compound

Product 1

HCID 22903535HCID 22903535, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 7-chloro-1-{6-[2-(3-ethoxycarbonylpropoxy)benzoyl-amino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (2.5 g)in ethylene glycol dimethyl ether (70 ml)is added sodium trimethoxyborohydride (3.78 g), and the mixture is refluxed for 3 hours. The reaction solution is gradually poured into diluted hydrochloric acid, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography, and recrystallized from dichloromethane-diethyl ether to give 7-chloro-1-{6-[2-(4-hydroxybutoxy)benzoylamino]nicotinoyl}-2,3,4,5-tetrahydro-1H-benzazepine (1.12 g) as white powder.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography
  8. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-b08d08924b71414d9c0b632494300ecc
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05498609

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes