Triethylamine → 4-(4-Benzyloxycarbonylamino-4-methyl-piperidine-1-carbonyl)benzoic Acid Methyl Ester

HRID 475359Notes

Reaction equation

HRID 475359 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:19])[NH:11][C:12]1([CH3:18])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH3:30][O:29][C:27](=[O:28])[C:26]1[CH:31]=[CH:32][C:23]([C:21]([N:15]2[CH2:16][CH2:17][C:12]([NH:11][C:10]([O:9][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:19])([CH3:18])[CH2:13][CH2:14]2)=[O:22])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 24728615Benzyl (4-methylpiperidin-4-yl)carbamate hydrochloride

Product 1

HCID 667570404-(4-Benzyloxycarbonylamino-4-methyl-piperidine-1-carbonyl)benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (4-methyl-piperidin-4-yl)-carbamic acid benzyl ester hydrochloride salt (0.15 g, 0.53 mmol, Example 30B) in dichloromethane (3 mL) at room temperature was added methyl 4-chlorocarbonylbenzoate (0.125 g, 0.62 mmol) and triethylamine (0.17 mL, 1.2 mmol). The reaction mixture was stirred at room temperature for 3 hours, aqueous ammonium chloride was added, and the mixture was extracted with dichloromethane (2×). The combined organic layers were washed with 10% KHSO4, sat. NaHCO3, brine, dried (MgSO4), and concentrated under reduced pressure to provide the titled compound. MS (CI) m/z 411 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 8.07 (d, 2H), 7.46 (d, 2H), 7.33 (m, 5H), 5.06 (s, 2H), 4.63 (m, 1H—NH), 4.18-4.13 (m, 2H), 3.95 (s, 3H), 3.36 (m, 2H), 2.09 (m, 2H), 1.78-1.42 (m, 2H), 1.41 (s, 3H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×)
  2. washThe combined organic layers were washed with 10% KHSO4, sat. NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a07a5e1ce3be4afa92012e8d58ae7ee5
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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