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Sodium → 7-benzyl-4-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine

HRID 400437
Notes
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Reaction equation

HRID 400437 reaction equation
[Na].Cl.[CH:3]([NH2:5])=[NH:4].[CH2:6]([N:13]1[CH2:19][CH2:18][C:17](Cl)=[C:16]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[CH2:6]([N:13]1[CH2:14][CH2:15][C:16]2[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:4][CH:3]=[N:5][C:17]=2[CH2:18][CH2:19]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 69190815(1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanone

Product 1

HCID 866860407-benzyl-4-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepineYield 39.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
6 °C

Procedure

16.8 g sodium was added to 500 mL ethanol at 10° C. Then, 48.5 g formamidine hydrochloride was added and the reaction was stirred 15 min at 6° C. 28 g (1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanone was added and the reaction was stirred 17.5 h at RT and 1 h at 40° C. The mixture was filtered and the solvent was removed. The residue was dissolved in ethyl acetate. The layers were separated and the organic layer was washed with water and evaporated. The residue was crystalysed with diethylether to yield 10.7 g of the desired product. Fp: 81-82° C.

Workup

  1. stirringthe reaction was stirred 17.5 h at RT and 1 h at 40° C
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. customevaporated

Sources & evidence

ORD record
ord-d8ddfc66d069496abd550205319993e9
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741892B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes