Acetic Acid → Benzyl 3-(4-methylpiperazin-1-yl)azetidine-1-carboxylate

HRID 1430810Notes

Reaction equation

HRID 1430810 reaction equation
O=[C:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH:2]2[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])[CH2:3]2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 10632047Benzyl 3-oxoazetidine-1-carboxylate

Product 1

HCID 86708494Benzyl 3-(4-methylpiperazin-1-yl)azetidine-1-carboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

A mixture of benzyl 3-oxoazetidine-1-carboxylate (1.026 g, 5 mmol), 1-methylpiperazine (0.833 mL, 7.50 mmol) and acetic acid (0.429 mL, 7.50 mmol) in 1,2-dichloroethane (5 mL) was stirred at room temperature for 3 h. sodium triacetoxyborohydride (2.119 g, 10.00 mmol) was added and the reaction mixture was stirred at room temperature overnight. A small amount of water was added to the reaction mixture and the reaction mixture was directly loaded onto a 120 g ISCO column and eluted with 1-12% 2N ammonia in methanol/dichloromethane). benzyl 3-(4-methylpiperazin-1-yl)azetidine-1-carboxylate (1.45 g) was obtained as a brown oil.

Workup

  1. additionwas added
  2. washeluted with 1-12% 2N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-f64d3d7ff1ca47f39db761ca5fcf9eb5
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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