Formaldehyde → HCID 67442441, compound

HRID 1667322Notes

Reaction equation

HRID 1667322 reaction equation
C=O.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1/[CH:11]=[CH:12]/[CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:28])[CH2:20][NH:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:15][CH2:14]1.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl:48]C(Cl)C>C(Cl)(Cl)Cl.C(O)(=O)C>[ClH:48].[CH3:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH3:3])[C:5]=1/[CH:11]=[CH:12]/[CH:13]1[CH2:14][CH2:15][N:16]([C:19](=[O:28])[CH2:20][N:21]([CH3:29])[CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH2:17][CH2:18]1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 63651,1-DichloroethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67443162HCID 67443162, compound

Product 1

HCID 67442441HCID 67442441, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

454 μl of 37% aqueous formaldehyde solution and 175 μl of acetic acid were added to a solution of 219 mg of (2-{4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidin-1-yl}-2-oxoethyl)tetrahydro-2H-pyran-4-ylamine in 5 ml of dichloroethane, followed by stirring at ambient temperature for 2 hours. Subsequently, 388 mg of sodium triacetoxyborohydride was added to the reaction mixture, followed by stirring at ambient temperature for 1 hour. Saturated aqueous sodium hydrogencarbonate solution and chloroform were added to the mixture, then the organic layer was fractionated and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol-ammonia water). The resulting oil was dissolved in 5 ml of ethanol, and 172 μl of 4N hydrochloric acid-ethyl acetate was added to the mixture. The solvent was evaporated under reduced pressure. The residue was crystallized from 2-propanol-diisopropyl ether. The crystals were recrystallized from 2-propanol-diisopropyl ether to give 201 mg of (2-{4-[(E)-2-(2,6-dimethylphenyl)vinyl]piperidin-1-yl}-2-oxoethyl)methyl(tetrahydro-2H-pyran-4-yl)amine monohydrochloride.

Workup

  1. stirringby stirring at ambient temperature for 1 hour
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (chloroform-methanol-ammonia water)
  4. dissolutionThe resulting oil was dissolved in 5 ml of ethanol
  5. addition172 μl of 4N hydrochloric acid-ethyl acetate was added to the mixture
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was crystallized from 2-propanol-diisopropyl ether
  8. customThe crystals were recrystallized from 2-propanol-diisopropyl ether

Sources & evidence

ORD record
ord-44d159e687a14991b5be810ef5f46ac6
Source dataset
uspto-grants-2011_10
Patent number
US08044206B2

Reaction notes

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