Acetic Acid → 1-Carbethoxy-4-dimethylamino-3-methylpiperidine

HRID 746855노트

반응식

HRID 746855 반응식
C=O.N[CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[CH3:15].[C:16]([BH3-])#[N:17].[Na+].[C:20](O)(=O)C>CO>[C:10]([N:7]1[CH2:8][CH2:9][CH:4]([N:17]([CH3:16])[CH3:20])[CH:5]([CH3:15])[CH2:6]1)([O:12][CH2:13][CH3:14])=[O:11]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22278886Ethyl 4-amino-3-methylpiperidine-1-carboxylate

생성물 1

HCID 222788651-Carbethoxy-4-dimethylamino-3-methylpiperidine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Paraformaldehyde (5.1 g) was added to the stirred solution of 4-amino-1-carbethoxy-3-methylpiperidine (3.5 g, 18.8 mmol) in methanol (100 ml) at 0° C. and sodium cyanoborohydride (1.7 g, 27.0 mmol) was added to it. Then, acetic acid (1 ml) was added to the resulting mixture and stirring was continued for 96 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH ˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give 1-carbethoxy-4-dimethylamino-3-methylpiperidine. Yield 3.5 g (88%), C11H22N2O2, m/z 215 (M+1).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with water
  3. extractionextracted with ethyl acetate
  4. customto remove impurities
  5. extractionextracted with ethyl acetate
  6. extractionEthyl acetate extract
  7. dry with materialwas dried (Na2SO4)
  8. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-3d24d65518384ac2936c5b061b0cb5fb
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393957B2

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