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Hydrazine hydrate (1:1) → (3aR*,10aS*)-4-(Aminoacetyl)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356162
Notes
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Reaction equation

HRID 356162 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[N:11]([C:19](=[O:32])[CH2:20][N:21]2C(=O)C3=CC=CC=C3C2=O)[C:10]2[CH:33]=[CH:34][CH:35]=[CH:36][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.ClCCl.C(OC(C)C)(C)C>C(O)C>[NH2:21][CH2:20][C:19]([N:11]1[C@@H:12]2[CH2:18][CH2:17][CH2:16][C@@H:13]2[C:14](=[O:15])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:36]=[CH:35][CH:34]=[CH:33][C:10]1=2)=[O:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 22238436Dichloromethane diisopropyletherHCID 70113585(3aR*,10aS*)-9-benzyl-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

Product 1

HCID 70110459(3aR*,10aS*)-4-(Aminoacetyl)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of (3aR*,10aS*)-9-benzyl-4-(phthalimidoacetyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (9.82 g, 20 mmol) and hydrazine monohydrate (2.31 g, 46 mmol) in ethanol (200 mL) was refluxed for 3.5 hours. The reaction mixture was cooled, which was subjected to filtration. The filtrate was washed with chloroform, which was concentrated under reduced pressure. The concentrate was suspended in chloroform, which was again subjected to filtration. The filtrate was concentrated under reduced pressure. The concentrate was crystallized from dichloromethane-hexane to give 5.62 g (yield 80%). The sample for analytical experiment was prepared by recrystallization from dichloromethane-diisopropylether. m.p. 163°-165° C.

Workup

  1. temperaturewas refluxed for 3.5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationwhich was subjected to filtration
  4. washThe filtrate was washed with chloroform, which
  5. concentrationwas concentrated under reduced pressure
  6. filtrationwhich was again subjected to filtration
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe concentrate was crystallized from dichloromethane-hexane
  9. customto give 5.62 g (yield 80%)

Sources & evidence

ORD record
ord-1808f9e6f91a4d5e9a91a0c226f17b4c
Source dataset
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834463

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes