Acetic Acid → HCID 44252387, 화합물

HRID 1477194노트

반응식

HRID 1477194 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 44252387HCID 44252387, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7399425ebb24445fa510b992e11ae566
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403767B2

반응 노트

불러오는 중…