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

HRID 1193364노트

반응식

HRID 1193364 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-fc5bfd6b36bd48b9968d2c27ed928998
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680159B2

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