Acetic Acid → HCID 18919742, compound

HRID 1291108Notes

Reaction equation

HRID 1291108 reaction equation
N[C:2]1[CH:23]=[CH:22][C:5]([C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.C=O.[BH3-][C:27]#[N:28].[Na+].[C:30](O)(=O)C>C(#N)C.CCOCC>[CH3:30][N:28]([CH3:27])[C:2]1[CH:23]=[CH:22][C:5]([C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 18919886HCID 18919886, compound

Product 1

HCID 18919742HCID 18919742, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

0.1025 g (0.00033 mol) of 1-benzyl-piperidin-4-yl 4-amino-benzoate was dissolved in 5 ml of acetonitrile and treated with 0.4 ml (0.0053 mol) of formaldehyde (37%) and 0.113 g (0.001534 mol) of NaBH3CN. The pH was adjusted to 6 with glacial acetic acid and the reaction mixture was stirred at 50° for 1 hr. Subsequently, the mixture was diluted with 25 ml of ether, washed with saturated bicarbonate solution and saturated sodium chloride solution and the org. phase was dried over magnesium sulfate. After removing the solvent the residue was chromatographed over silica gel with dichloromethane/methanol (19:1). 0.078 g (70%) of 1-benzyl-piperidin-4-yl 4-dimethylamino-benzoate was obtained as white crystals; m.p. 103°.

Workup

  1. washwashed with saturated bicarbonate solution and saturated sodium chloride solution
  2. dry with materialphase was dried over magnesium sulfate
  3. customAfter removing the solvent the residue
  4. customwas chromatographed over silica gel with dichloromethane/methanol (19:1)

Sources & evidence

ORD record
ord-95c244fe06a44dcab7b822c03eabe66d
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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