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Dicyclohexylcarbodiimide → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide

HRID 908962
ノート
印刷プレビュー

反応式

HRID 908962 の反応式
Cl.[CH3:2][N:3]([CH3:20])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([OH:13])=O)[CH2:6][CH2:5]1.C1(N=[C:28]=[N:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:20][N:3]([CH3:2])[C:4]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:5][CH2:6][CH:7]([CH2:10][C:11]([NH:3][CH2:4][CH2:5][C:6]2[C:31]3[C:30](=[CH:35][CH:34]=[CH:33][CH:32]=3)[NH:29][CH:28]=2)=[O:13])[CH2:8][CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 673861314-Dimethylamino-4-phenylcyclohexyl-acetic acid hydrochloride

生成物 1

HCID 115394472-(4-Dimethylamino-4-phenylcyclohexyl)-N-[2-(1H-indol-3-yl)ethyl]acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

実験手順

(4-dimethylamino-4-phenylcyclohexyl)acetic acid hydrochloride (298 mg, 1.0 mmol) in dry dimethylformamide under argon. The clear solution was cooled in an ice-bath and dicyclohexylcarbodiimide (417 mg, 2.0 mmol) was added. The reaction mixture was stirred at RT for 3 d and worked up by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). The mixture was diluted with water, 5 M sodium hydroxide solution (4 ml, 20 mmol) was added and the mixture was stored at 5° C. for 16 h. The crude product thereby precipitated out as a beige-coloured substance (400 mg). After purification by chromatography on silica gel with methanol, the product was obtained as a beige-coloured solid in a yield of 35% (144 mg) and with an m.p.

後処理

  1. temperatureThe clear solution was cooled in an ice-bath
  2. customby separating off the urea which
  3. customhad precipitated out
  4. additionintroducing the filtrate
  5. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  6. additionwas added
  7. waitthe mixture was stored at 5° C. for 16 h
  8. customThe crude product thereby precipitated out as a beige-coloured substance (400 mg)
  9. customAfter purification by chromatography on silica gel with methanol
  10. customthe product was obtained as a beige-coloured solid in a yield of 35% (144 mg) and with an m.p.

出典と根拠

ORDレコード
ord-037ec87b29b74a35a1aa2e78728dd51e
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017630B2

反応ノート

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