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Triethylamine → HCID 18001097, compound

HRID 478355
Notes
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Reaction equation

HRID 478355 reaction equation
[C:1]([CH2:4][CH:5]1[C:11]2[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=2[N:9]([C:17](=[O:30])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:8][CH2:7][CH2:6]1)([OH:3])=O.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[CH3:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1.C(N(CC)CC)C>ClCCl.O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]2[N:9]([C:17](=[O:30])[C:18]3[CH:19]=[CH:20][C:21]([CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:22][CH:23]=3)[CH2:8][CH2:7][CH2:6][CH:5]([CH2:4][C:1]([N:50]3[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]3)=[O:3])[C:11]=2[CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 18001027HCID 18001027, compound

Product 1

HCID 18001097HCID 18001097, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-carboxymethyl-7-chloro-1-(4-cyclohexylbenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.7 g) in dichloromethane (50 ml) is added with stirring N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (0.54 g) under ice-cooling, and the mixture is stirred at room temperature for 15 minutes. To the mixture are added with stirring N-methylpiperazine (0.24 ml) and triethylamine (0.46 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. To the reaction solution is added water, and the mixture is extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=40:1) to give 7-chloro-5-[(4-methyl-1-piperazinyl)carbonylmethyl]-1-(4-cyclohexylbenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.7 g) as colorless amorphous.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature overnight
  4. extractionthe mixture is extracted with dichloromethane
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=40:1)

Sources & evidence

ORD record
ord-a88f0d99b363405d8ce557734277ff95
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes