Hydrazine hydrate (1:1) → HCID 19607839, compound

HRID 1603107Notes

Reaction equation

HRID 1603107 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:40]=[CH:39][CH:38]=[CH:37][C:14]=2[C:15]([NH:17][C:18]2[CH:36]=[CH:35][C:21]([C:22]([N:24]3[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])=[CH:20][CH:19]=2)=[O:16])C(=O)C2=CC=CC=C12.O.NN>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:40]=[CH:39][CH:38]=[CH:37][C:14]=1[C:15]([NH:17][C:18]1[CH:36]=[CH:35][C:21]([C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[CH:20][CH:19]=1)=[O:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19607843HCID 19607843, compound

Product 1

HCID 19607839HCID 19607839, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-{4-[2-[6-phthalimidohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (3.75 g), hydrazine hydrate (0.44 ml) and ethanol (30 ml) is refluxed for 3.5 hours. The precipitated crystal is collected by filtration, dried and purified by silica gel column chromatography (eluent; chloroform:methanol:aqueous ammonia=100:10:1), and recrystallized from methanol/diethyl ether to give 1-{4-[2-(6-aminohexyloxy)benzoylamino]benzoyl}-2,3,4,5-tetrahydro-1H-benzazepine (2.52 g) as white powder, m.p. 135.5-137.5° C.

Workup

  1. temperatureis refluxed for 3.5 hours
  2. filtrationThe precipitated crystal is collected by filtration
  3. customdried
  4. custompurified by silica gel column chromatography (eluent; chloroform:methanol:aqueous ammonia=100:10:1)
  5. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-6378aec85d8246b7b3cf46af4127f155
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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