Sodium Hydroxide → 1-(1-Benzyl-4-methylpiperazin-2-yl)methanamine

HRID 902054Notes

Reaction equation

HRID 902054 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][N:17]([C:20](OC(C)(C)C)=O)[CH2:16][CH:15]1[C:27](=O)[NH2:28])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[NH2:28][CH2:27][CH:15]1[CH2:16][N:17]([CH3:20])[CH2:18][CH2:19][N:14]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 69206757HCID 69206757, compound

Product 1

HCID 117756161-(1-Benzyl-4-methylpiperazin-2-yl)methanamineYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

1M Lithium aluminium hydride in tetrahydrofuran (112 ml, 0.112 mol) was added dropwise to a stirred solution of (RS)-1-benzyl-4-(tert-butyloxycarbonyl)-2-carbamoylpiperazine (D1) (15 g, 0.047 mol) in anhydrous tetrahydrofuran (300 ml) at room temperature under argon. On complete addition the reaction mixture was stirred at room temperature for 0.5 h, then at reflux for a further 1.5 h. The mixture was cooled to room temperature and treated sequentially with water (19.5 ml), 2N sodium hydroxide (22.5 ml) and water (19.5 ml) dropwise. Sodium sulphate was added and the resultant stirred for 0.3 h, filtered and the filtrate evaporated in vacuo to give the title compound (10.3 g, 100%).

Workup

  1. additionOn complete addition the reaction mixture
  2. temperatureat reflux for a further 1.5 h
  3. temperatureThe mixture was cooled to room temperature
  4. stirringthe resultant stirred for 0.3 h
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-232abf793bbc4b57b0d5e3745a447d4d
Source dataset
uspto-grants-2008_04
Patent number
US07365077B2

Reaction notes

Loading…