Triethylamine → HCID 18001097, compound

HRID 1870447Notes

Reaction equation

HRID 1870447 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

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 962WaterSolventHCID 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-62270d04a957416da4c5d6de76a1141c
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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