Triethylamine → HCID 70062657, compound

HRID 1291647Notes

Reaction equation

HRID 1291647 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-d0b545a537fd48a4bc3099b19999a3e5
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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