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

HRID 1291628Notes

Reaction equation

HRID 1291628 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-1491c271910247ec98967b8dce3c340f
Source dataset
uspto-grants-1998_05
Patent number
US05753677

Reaction notes

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