Tetrahydrofuran → Phenylmethyl 4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate

HRID 1457611Notes

Reaction equation

HRID 1457611 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.C1COCC1>O>[CH2:1]([O:8][C:9]([N:12]1[CH2:13][CH2:14][CH:15]([CH2:18][NH:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:17]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 16004294N-(Phenylmethyl)-4-piperidinemethanamine

Product 1

HCID 22099453Phenylmethyl 4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 3.46 g of benzyloxycarbonyl chloride was added dropwise to a mixed solution of 4.15 g of N-(4-piperidylmethyl)-N-benzylamine, 2.10 g of triethylamine and 200 ml of THF. After stirring the mixture at the same temperature for 3 hours and then at room temperature for 2 hours, water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent; chloroform:methanol=19:1) to give 3.41 g of N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-N-benzylamine (yield: 50%, IR: 1702 cm-1).

Workup

  1. temperatureUnder ice-cooling
  2. waitat room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (solvent; chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-ef52abcfdcbe4472953f7438bd2c445b
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

Loading…