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

HRID 1193364Notes

Reaction equation

HRID 1193364 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)

Workup

  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)

Sources & evidence

ORD record
ord-fc5bfd6b36bd48b9968d2c27ed928998
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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