Toluene → N-ethyl-2-(2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

HRID 224420

反応式

HRID 224420 の反応式
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:8]=1[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:25][CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:32][CH3:33]>CC(CC)=O>[ClH:3].[CH2:32]([N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[CH2:26][NH:25][C:9](=[O:11])[C:8]1[C:12]([O:16][CH3:17])=[CH:13][CH:14]=[CH:15][C:7]=1[O:6][CH3:5])[CH3:33]

参加物

6

反応物 4

HCID 1140TolueneHCID 151092,6-Dimethoxybenzoic AcidHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidine

生成物 1

HCID 15565705N-ethyl-2-(2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

30 ml of thionyl chloride is added to 18.2 g (0.1 mol) of 2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 12.8 g (0.1 mol) of 2-(aminomethyl)-1-ethyl-pyrrolidine in 50 ml methylethyl ketone. After the addition the mixture is stirred for 30 minutes at room temperature. The obtained precipitate is filtered off, washed with ether and recrystallized from ethanol - isopropyl ether. Yield: 26.7 g, m.p. 182°-84° C.

後処理

  1. temperatureThe mixture is heated on a steam bath for 30 minutes
  2. customThe solvent and excess thionyl chloride is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in 50 ml of dry methyl ethyl ketone
  4. additionThe solution is added dropwise
  5. additionAfter the addition the mixture
  6. filtrationThe obtained precipitate is filtered off
  7. washwashed with ether
  8. customrecrystallized from ethanol - isopropyl ether

出典と根拠

ORDレコード
ord-7acfa7c2db2a4f08802a8102cb5cfeb8
出典データセット
uspto-grants-1980_11
特許番号
US04232037

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