Phosphoric Acid → Memantine

HRID 899576

反応式

HRID 899576 の反応式
Br[C:2]12[CH2:11][C:6]3([CH3:12])[CH2:7][CH:8]([CH2:10][C:4]([CH3:13])([CH2:5]3)[CH2:3]1)[CH2:9]2.[NH2:14]C(N)=O.P(=O)(O)(O)O.[OH-].[K+]>C(O)=O>[NH2:14][C:2]12[CH2:11][C:6]3([CH3:12])[CH2:7][CH:8]([CH2:10][C:4]([CH3:13])([CH2:5]3)[CH2:3]1)[CH2:9]2

参加物

6

反応物 4

HCID 1004Phosphoric AcidHCID 1176UreaHCID 14797Potassium HydroxideHCID 983171-Bromo-3,5-dimethyladamantane

生成物 1

HCID 4054Memantine

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
80 °C

実験手順

To 100 g of 1-bromo-3,5-dimethyl adamantane and 86 g of urea, adding 80 ml of 80 wt % formic acid, heating to 80° C. and holding for 3 hours. Cooling to the room temperature and adding 75 ml of 85% phosphoric acid to hydrolyze at 80° C. for 1 hour. Adjusting with 10% potassium hydroxide aqueous solution to a pH of 12. Extracting with toluene twice, combining the organic layers and washing with water. Concentrating under reduced pressure to yield a limpid yellow solution as 1-amino-3,5-dimethyl adamantane crude. To the crude, adding 150 ml of ethanol and concentrated hydrochloric acid, heating to dissolve and crystallizing to yield a white solid. Drying the solid and re-crystallizing with ethanol to yield 61.0 g of pure Memantine Hydrochloride. The yield is 68.8% (GC 99.5%).

後処理

  1. temperatureCooling to the room temperature
  2. waitto hydrolyze at 80° C. for 1 hour
  3. extractionExtracting with toluene twice
  4. washwashing with water
  5. concentrationConcentrating under reduced pressure

出典と根拠

ORDレコード
ord-513daf0fcba7481688f792b5bd4a0297
出典データセット
uspto-grants-2008_04
特許番号
US07355080B2

関連ノート

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