Tetrahydrofuran → 4-[(2,2-Diethoxyethyl)thio]-1-methylpiperidine

HRID 36883

反応式

HRID 36883 の反応式
C[O-].[Na+].[CH3:4][N:5]1[CH2:10][CH2:9][CH:8]([SH:11])[CH2:7][CH2:6]1.Br[CH2:13][CH:14]=[O:15].[O:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH2:14]([O:15][CH:17]([O:16][CH2:20][CH3:19])[CH2:18][S:11][CH:8]1[CH2:9][CH2:10][N:5]([CH3:4])[CH2:6][CH2:7]1)[CH3:13]

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 105131Acetaldehyde, bromo-HCID 10942334Sodium MethoxideHCID 141803911-Methylpiperidine-4-thiol

生成物 1

HCID 199366074-[(2,2-Diethoxyethyl)thio]-1-methylpiperidine

反応条件

温度
40 °C

実験手順

Sodium methylate (18.1 g) is added in portions to a solution of 1-methylpiperidine-4-thiol (22 g) in anhydrous tetrahydrofuran (200 ml). After one hour, the diethyl acetal of bromoacetaldehyde (30.3 ml) is added. After 4 hours at room temperature, the solution is heated for 2 hours at 40° C. The insoluble material is filtered off and rinsed with THF. The filtrate is concentrated and then distilled under reduced pressure to give 4-[(2,2-diethoxyethyl)thio]-1-methylpiperidine (36 g; b.p.=104°-108° C. under 0.05 atm) in the form of an oil.

後処理

  1. waitAfter 4 hours at room temperature
  2. filtrationThe insoluble material is filtered off
  3. washrinsed with THF
  4. concentrationThe filtrate is concentrated
  5. distillationdistilled under reduced pressure

出典と根拠

ORDレコード
ord-0036740931ac42919ebbc0deb994d2c7
出典データセット
uspto-grants-1995_05
特許番号
US05418242

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