Hydrochloric Acid → 4-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

HRID 228038ノート

反応式

HRID 228038 の反応式
C(OC([NH:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([N:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([N:19]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH3:20])=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 231505174-tert-butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

生成物 1

HCID 231507454-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

4-tert-Butoxycarbonylamino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (80.0 mg) was mixed with a 4 mol/L dioxane solution of hydrogen chloride (1.2 mL) and the mixture was stirred at room temperature for 40 minutes. The crystallized product was collected by filtration and was suspended in water (0.8 mL). While the suspension was chilled in an ice bath, a 1 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added and the mixture was extracted with dichloromethane (4×3 mL). The dichloromethane extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This gave 4-amino-N-(4-chlorophenyl)-N-methylbicyclo[2.2.2]octane-1-carboxamide (39.8 mg) as a white solid.

後処理

  1. filtrationThe crystallized product was collected by filtration
  2. temperatureWhile the suspension was chilled in an ice bath
  3. additiona 1 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added
  4. extractionthe mixture was extracted with dichloromethane (4×3 mL)
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-6d266e79336e437e84ad20eda97aaad6
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

反応ノート

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