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Formaldehyde → HCID 18001025, compound

HRID 478371
Notes
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Reaction equation

HRID 478371 reaction equation
[N:1]1([C:7]2[CH:25]=[CH:24][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[C:9]([Cl:26])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C=O.N1C2C=CC=CC=2CCC[CH2:30]1.[Na].[Na]>C(OCC)(=O)C>[CH3:30][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:25]=[CH:24][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[C:9]([Cl:26])[CH:8]=2)[CH2:2][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 5360545SodiumHCID 18001092HCID 18001092, compoundHCID 70033094HCID 70033094, compound

Product 1

HCID 18001025HCID 18001025, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To a mixture of 1-[4-(1-piperazinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g), 37% formaldehyde (0.45 g) and sodium tetrahydro-1H-benzazepine (0.25 g), 37% formaldehyde (0.45 g) and sodium (0.12 g) under ice-cooling, and the mixture is stirred at room temperature for one hour. To the reaction solution is added ethyl acetate, and the mixture is washed with a 2N aqueous sodium hydroxide solution and distilled water. The organic layer is dried over magnesium sulfate, filtered, and concentrated, and the resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=10:1) to give 1-[4-(4-methyl-1-piperazinyl)-2-chlorobenzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.10 g) as white powder.

Workup

  1. temperaturecooling
  2. washthe mixture is washed with a 2N aqueous sodium hydroxide solution
  3. distillationdistilled water
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe resulting residue is purified by silica gel column chromatography (solvent; dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-170a33be0fb1413b8a5c1844ac81996f
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06642223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes