Triethylamine → HCID 69961279, compound

HRID 1870460Notes

Reaction equation

HRID 1870460 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[C:4]([Cl:21])[CH:3]=1.Cl[C:23](Cl)([O:25][C:26](=[O:32])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[N:41]1[CH:46]=[CH:45][C:44](CO)=[CH:43][CH:42]=1>ClC1C=CC=CC=1Cl.C(OCC)(=O)C>[N:41]1[CH:46]=[CH:45][C:44]([CH2:23][O:25][C:26]([NH:1][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])=[C:4]([Cl:21])[CH:3]=2)=[O:32])=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 114724-HydroxymethylpyridineHCID 94429TriphosgeneHCID 10828112HCID 10828112, compound

Product 1

HCID 69961279HCID 69961279, compoundYield 117.8%

Reagents, catalysts & solvents 2

HCID 72391,2-DichlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-(4-amino-2-chlorobenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.8 g) in o-dichlorobenzene (5 ml) is added triphosgen (0.26 g), and the mixture is stirred at 120° C. for three hours. To the mixture is added triethylamine (0.27 g), and the mixture is stirred at 120° C. for two hours. To the mixture is added (4-pyridyl)methanol (0.29 g), and the mixture is stirred at 120° C. for two hours. To the reaction solution is added ethyl acetate, and the mixture is washed with water, and the organic layer is dried over magnesium sulfate, filtered, and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:5→dichloromethane:methanol=25:1), and the residue is washed with methanol/diethyl ether to give 1-{4-[(4-pyridyl)methoxycarbonylamino]-2-chlorobenzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (0.45 g) as white powder.

Workup

  1. stirringthe mixture is stirred at 120° C. for two hours
  2. stirringthe mixture is stirred at 120° C. for two hours
  3. washthe mixture is washed with water
  4. dry with materialthe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto remove the solvent
  8. customThe resulting residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:5→dichloromethane:methanol=25:1)
  9. washthe residue is washed with methanol/diethyl ether

Sources & evidence

ORD record
ord-9056d50806614fd68d22d41ada505c23
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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