4-Aminobenzoic Acid → Tert-butyl 4-((4-aminobenzamido)methyl)piperidine-1-carboxylate

HRID 714988Notes

Reaction equation

HRID 714988 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>ClCCl>[NH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)=[O:22])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 79724-MethylmorpholineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59587665Tert-butyl 4-((4-aminobenzamido)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(aminomethyl)-Boc-piperidine (0.313 g, 1.458 mmol), 4-aminobenzoic acid (0.200 g, 1.458 mmol) and N-methyl morpholine (0.242 mL, 2.187 mmol) in dichloromethane (2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.422 g, 2.187 mmol) and the reaction mixture stirred at room temperature overnight. The reaction was then washed with water and brine. The organic phase was dried over MgSO4 and the solvent removed in vacuo. The residue was purified by silica gel column chromatography using a 0-100% EtOAc in hexane gradient to afford tert-butyl 4-((4-aminobenzamido)methyl)piperidine-1-carboxylate. LCMS (3) Rt: 1.91 min; m/z (ES+) 334.

Workup

  1. washThe reaction was then washed with water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-226a9e7bb439415ea52ea50fea74bc65
Source dataset
uspto-grants-2015_11
Patent number
US09187465B2

Reaction notes

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