Dimethylbarbituric acid → 4-Amino-1-benzylpiperidin-2-one

HRID 1257623Notes

Reaction equation

HRID 1257623 reaction equation
C([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[CH2:6]1)C=C.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[CH2:6]1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 673257434-(Allylamino)-1-benzylpiperidin-2-one

Product 1

HCID 534212544-Amino-1-benzylpiperidin-2-oneYield 72.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of racemic 4-allylamino-1-benzyl-piperidin-2-one (430 mg, 1.76 mmol), 1,3-dimethyl barbituric acid (824 mg 5.28 mmol) and Pd(PPh3)4 (204 mg, 0.18 mmol) in DCM (20 mL) was stirred at ambient temperature for 2 hours then concentrated under vacuum. The resulting residue was purified by Isolute® SCX-2 column (gradient: DCM to 5 to 60% 2M NH3 in methanol solution in DCM) to afford 260 mg (72%) of racemic 4-amino-1-benzyl-piperidin-2-one. LCMS (Method H, ESI): RT=0.35 min, m+H=204.9; 1H NMR (400 MHz, CDCl3) δ: 7.29 (m, 5H), 4.60 (m, 2H), 3.34-3.13 (m, 3H), 2.74 (ddd, 1H), 2.37-2.23 (m, 1H), 2.01 (m, 3H), 1.64 (m, 1H).

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe resulting residue was purified by Isolute® SCX-2 column (gradient: DCM to 5 to 60% 2M NH3 in methanol solution in DCM)

Sources & evidence

ORD record
ord-8496f61d4e1d4bc197627510ed6a5b9a
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…