HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 475371
Notes
Print preview

Reaction equation

HRID 475371 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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-b63e7cbe280941df97ff0e9613bc3a66
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637546B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes