Isatoic Anhydride → 2-amino-N-methyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362905ノート

反応式

HRID 362905 の反応式
[CH3:1][NH:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:5]1.[C:23]12[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=1)[NH:28]C(=O)[O:26][C:24]2=O.C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.CN(C=O)C>[NH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:23]=1[C:24]([N:2]([CH3:1])[CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)=[O:26]

参加物

6

反応物 3

HCID 8359Isatoic AnhydrideHCID 516892Sodium BicarbonateHCID 537192494-(N-methylamino)methyl-1-diphenylmethylpiperidine

生成物 1

HCID 675951382-amino-N-methyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide収率 67%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

Step 3): A solution of 4-(N-methylamino)methyl-1-diphenylmethylpiperidine (1.8 g, 6.0 mmol), isatoic anhydride (0.9 g, 5.5 mmol) and 4-dimethylaminopyridine (0.74 g) in DMF (25 ml) was stirred at room temperature for 2 hours. The reaction mixture was poured into 1% NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate and hexane) to give 2-amino-N-methyl-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (1.5 g, 67%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate and hexane)

出典と根拠

ORDレコード
ord-04f806f826cd45c79ee9fdcb12f08b60
出典データセット
uspto-grants-1999_02
特許番号
US05872115

反応ノート

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