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

HRID 1865228ノート

反応式

HRID 1865228 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9e188b07a10e4ff68d6a24ba9a8f003c
出典データセット
uspto-grants-2009_12
特許番号
US07626032B2

反応ノート

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