Benzylamine → N-Benzyl 1-boc-piperidine-4-carboxamide

HRID 83656Notes

Reaction equation

HRID 83656 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH2:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N(CC)CC)C>C(Cl)Cl.O.C(OCC)(=O)C>[CH2:38]([NH:45][C:14]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)=[O:16])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

9

Reactant 5

HCID 7504BenzylamineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 16467162N-Benzyl 1-boc-piperidine-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (10.41 g, 45.4 mmol), HOBT (13.91 g, 91 mmol), and EDCI (17.41 g, 91 mmol) were dissolved in DCM (Volume: 150 ml). The reaction was stirred for twenty minutes before benzylamine (9.92 ml, 91 mmol) and triethylamine (18.99 ml, 136 mmol) were added. The reaction was allowed to overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via column chromatography using 0-50% ethyl acetate:hexanes to obtain a white solid. (Yield: 6.9 g, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.32, 7.329-7.207, 4.25, 3.96-3.93, 2.72, 2.38-2.32, 1.70-1.67, 1.48-1.37

Workup

  1. additionwere added
  2. washThe organic layer was washed with saturated sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified via column chromatography
  7. customhexanes to obtain a white solid

Sources & evidence

ORD record
ord-47dbc0c6df4947e39b807f1830b2ce71
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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