Triethylamine → (4-Methyl-1-(pyridine-4-carbonyl)-piperidin-4-yl)-carbamic acid benzyl ester

HRID 1642689Notes

Reaction equation

HRID 1642689 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.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH2:2]([O:9][C:10](=[O:19])[NH:11][C:12]1([CH3:18])[CH2:17][CH2:16][N:15]([C:20]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[O:27])[CH2:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 417436Pyridine-4-carbonyl chlorideHCID 24728615Benzyl (4-methylpiperidin-4-yl)carbamate hydrochloride

Product 1

HCID 66757104(4-Methyl-1-(pyridine-4-carbonyl)-piperidin-4-yl)-carbamic acid benzyl 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 isonicotinoyl chloride (0.4 g, 2.79 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×). Combined organic layers were washed with 10% KHSO4, sat. NaHCO3, and brine before drying (MgSO4), and concentration under reduced pressure to provide (4-methyl-1-(pyridine-4-carbonyl)-piperidin-4-yl)-carbamic acid benzyl ester. MS (CI) m/z 354 (M+1)+; 1H NMR (300 MHz, CDCl3) δ ppm 8.69 (d, 2H), 7.40-7.31 (m, 7H), 5.06 (s, 2H), 4.15 (m, 1H), 4.62 (m, 4H), 2.12 (m, 2H), 1.77-1.45 (m, 2H), 1.42 (s, 3H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×)
  2. washCombined organic layers were washed with 10% KHSO4, sat. NaHCO3, and brine
  3. custombefore drying
  4. concentration(MgSO4), and concentration under reduced pressure

Sources & evidence

ORD record
ord-34353c33fe8b4bd1a002a12fe026af9b
Source dataset
uspto-grants-2012_02
Patent number
US08119664B2

Reaction notes

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