Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Hydroxymethylpyridine | HCID 11472 | — |
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | HCID 10828112 | HCID 10828112 | — |
| Solvent | 1,2-Dichlorobenzene | HCID 7239 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69961279 | HCID 69961279 | 117.8% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06642223B2 |
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| Source dataset | uspto-grants-2003_11 |
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| ORD ID | ord-e0f8fc539e534732bf3645aeaa9bdae3 |
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| Source note | uspto-grants-2003_11 |
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