Sodium cyanoborohydride → N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine

HRID 1193364ノート

反応式

HRID 1193364 の反応式
[CH2:1]([N:8]([CH3:16])[CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[CH2:19]1[C:28]2[C:23](=[CH:24][N:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][NH:20]1.[BH3-]C#N.[Na+]>CO>[CH2:1]([N:8]([CH3:16])[CH:9]1[CH2:14][CH2:13][CH:12]([N:25]2[CH2:26][CH2:27][C:28]3[C:23](=[CH:22][CH:21]=[N:20][CH:19]=3)[CH2:24]2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 220099204-[Benzyl(methyl)amino]cyclohexan-1-oneHCID 667992971,2,3,4-Tetrahydro-2,6-naphthyridine dihydrochloride

生成物 1

HCID 66799315N-Benzyl-4-(3,4-dihydro-2,6-naphthyridin-2(1H)-yl)-N-methylcyclohexanamine収率 38%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-(Benzyl(methyl)amino)cyclohexanone (680 mg, 3.133 mmol, 1.0 eq.) and 1,2,3,4-tetrahydro-2,6-naphthyridine dihydrochloride (713 mg, 3.44 mmol, 1.1 eq.) were dissolved in MeOH (20 ml) and the mixture was stirred for 5 hours at RT. Then the solution was cooled to 0° C., NaCNBH3 (393 mg, 3.26 mmol, 2.0 eq.) was added and the mixture was stirred for 16 hours at RT. The reaction solution was concentrated to dryness under reduced pressure and purified by column chromatography (Alox, 1.2% MeOH in DCM). Yield: 38% (400 mg, 1.194 mmol)

後処理

  1. temperatureThen the solution was cooled to 0° C.
  2. stirringthe mixture was stirred for 16 hours at RT
  3. concentrationThe reaction solution was concentrated to dryness under reduced pressure
  4. custompurified by column chromatography (Alox, 1.2% MeOH in DCM)

出典と根拠

ORDレコード
ord-fc5bfd6b36bd48b9968d2c27ed928998
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

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