Formaldehyde → HCID 70161017, compound

HRID 1251082Notes

Reaction equation

HRID 1251082 reaction equation
[F:1][C:2]1([F:37])[CH2:3][CH2:4][N:5]([C:23]([C:25]2[S:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:27][C:26]=2[CH3:36])=[O:24])[C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2/[C:8]/1=[CH:9]/[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].C=O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C>[F:37][C:2]1([F:1])[CH2:3][CH2:4][N:5]([C:23]([C:25]2[S:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:27][C:26]=2[CH3:36])=[O:24])[C:6]2[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=2/[C:8]/1=[CH:9]/[C:10]([NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH3:40])[CH2:17][CH2:18]1)=[O:11]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70161878HCID 70161878, compound

Product 1

HCID 70161017HCID 70161017, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 60 mg of (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]-N-(4-piperidyl)acetamide in 5 ml of dichloromethane were added 70 μl of a 40% aqueous solution of formaldehyde, 74 μl of acetic acid and 30 mg of sodium triacetoxy borohydride, followed by stirring at room temperature for six hours. To the reaction solution was added a saturated aqueous solution of sodium bicarbonate, followed by extracting with ethyl acetate. The organic layer was washed with a saturated aqueous solution of NaCl and dried over anhydrous magnesium sulfate, followed by evaporating the solvent therefrom. The residue was purified by silica gel column chromatography (eluting with chloroform) and crystallized from diethyl ether to give 53 mg of (Z)-[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]-N-(1methyl-4-piperidyl)acetamide as a colorless powder.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of NaCl
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customby evaporating the solvent
  5. customThe residue was purified by silica gel column chromatography (eluting with chloroform)
  6. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-c56cf13b62554ab48eaa88948bdc6218
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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