Methylamine → Ammonia

HRID 586707Notes

Reaction equation

HRID 586707 reaction equation
[CH3:1][NH2:2].[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[N:16]=[C:15](Cl)[CH:14]=[CH:13][C:12]=2[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[NH3:10].[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[N:16]=[C:15]([NH:2][CH3:1])[CH:14]=[CH:13][C:12]=2[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 162287476-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 2

HCID 222AmmoniaHCID 22335272HCID 22335272, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

Liquid methylamine (20 mL) was added to a cooled (−70° C.) solution of 6-benzyl-2-chloro-5,6,7,8-tetrahydro[1,6]naphthyridine (WO 9830560) (5.5 g, 21.25 mmol) in methanol (30 mL). The mixture was heated to 140° C. in a sealed vessel for 72 hours, then cooled. The reaction mixture was evaporated under reduced pressure and the residual brown oil purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (97:3:0 to 96:4:0.5) to afford the title compound as a white solid, 2.97 g

Workup

  1. temperaturecooled
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residual brown oil purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-142ee26f74054094ba078c2602f8ef70
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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