Triethylamine → HCID 70062657, compound

HRID 1603126Notes

Reaction equation

HRID 1603126 reaction equation
[O:1]1[CH:8]2[CH:2]1[CH2:3][CH2:4][N:5]([C:13](=[O:30])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[CH:16][CH:15]=1)[C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=12.Cl.[CH3:32][NH:33][CH3:34].C(N(CC)CC)C>CO>[CH3:32][N:33]([CH3:34])[C@@H:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([C:13](=[O:30])[C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:29])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[CH:18][CH:19]=2)[CH2:4][CH2:3][C@H:2]1[OH:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 19607898HCID 19607898, compound

Product 1

HCID 70062657HCID 70062657, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4,5-epoxy-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.5 g), dimethylamine hydrochloride (2.6 g), triethylamine (4.5 g) and methanol (15 ml) is refluxed for 19 hours. After completion of the reaction, the solvent is distilled off and the resulting residue is dissolved in dichloromethane. The mixture is washed successively with water and saturated saline solution. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1), and recrystallized from ethanol/diethyl ether to give trans-5-dimethylamino-4-hydroxy-1-[4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.38 g) as colorless needles, m.p. 180-182° C.

Workup

  1. temperatureis refluxed for 19 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent is distilled off
  4. dissolutionthe resulting residue is dissolved in dichloromethane
  5. washThe mixture is washed successively with water and saturated saline solution
  6. distillationThe solvent is distilled off
  7. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=50:1)
  8. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-c950b560428644b38bddbef77fb3ea54
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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