Triethylamine → N-(tert-butoxycarbonyl)piperidine

HRID 717072Notes

Reaction equation

HRID 717072 reaction equation
C(C1C=CC(S(Cl)(=O)=O)=CC=1)#N.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23](CNC)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(Cl)Cl>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 21934652tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 7010304N-(tert-butoxycarbonyl)piperidineYield 184%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-cyanobenzenesulfonyl chloride (411 mg, 2.2 mmol) in CH2Cl2 (10 mL) was added 4-methylaminomethyl-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.2 mmol) and triethylamine (0.91 mL, 6.5 mmol) and the reaction stirred at RT for 2 h after which time silica was added and solvent removed. The crude residue was purified by silica gel chromatography eluting with isohexane, and increasing the polarity to 100% EtOAc to afford 4{[4-cyano-benzenesulfonyl)-methyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester as a white solid (750 mg, 87%).

Workup

  1. additionwas added
  2. customsolvent removed
  3. customThe crude residue was purified by silica gel chromatography
  4. washeluting with isohexane
  5. temperatureincreasing the polarity to 100% EtOAc

Sources & evidence

ORD record
ord-bf46d1be6e45406da2989b06d1e653bb
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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