Acetic Acid → HCID 44252387, compound

HRID 1477194Notes

Reaction equation

HRID 1477194 reaction equation
[CH2:1]([C:8]1([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([NH:14][CH3:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:28](B)#N.[Na].C(O)(=O)C>C(#N)C>[CH2:1]([C:8]1([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:13][CH2:12][C:11]([N:14]([CH3:28])[CH3:15])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 686322714-benzyl-4-((dimethylamino)methyl)-N-methyl-1-phenylcyclohexanamineHCID 101953985CID 101953985

Product 1

HCID 44252387HCID 44252387, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the title compound from Example 33 (1.40 g, 4.16 mmol) and formalin (5.8 mL, 37% aqueous solution) in acetonitrile (40 mL) was mixed in portions with sodium cyanoboron hydride (1.03 g, 16.6 mmol) and stirred for 45 min at room temperature. Concentrated acetic acid was then added until a neutral reaction occurred and the mixture stirred for 45 min at room temperature. For work up the solvent was removed in a vacuum, the residue taken up in 2N NaOH (40 mL) and then extracted with ether (3×40 mL). The organic phase was dried over Na2SO4, filtered and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with ethyl acetate (methanol→methanol+2% TEA).

Workup

  1. stirringthe mixture stirred for 45 min at room temperature
  2. customFor work up the solvent was removed in a vacuum
  3. extractionextracted with ether (3×40 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to low volume in a vacuum
  7. customThe remaining residue was purified by flash chromatography with ethyl acetate (methanol→methanol+2% TEA)

Sources & evidence

ORD record
ord-7399425ebb24445fa510b992e11ae566
Source dataset
uspto-grants-2016_08
Patent number
US09403767B2

Reaction notes

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