tert-Butyl 4-carbamothioylpiperidine-1-carboxylate → 4-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine

HRID 1401841Notes

Reaction equation

HRID 1401841 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:11]([CH3:16])([CH3:15])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]=2[CH:6]=1)=O.C(OC([N:26]1[CH2:31][CH2:30][CH:29]([C:32](=[S:34])[NH2:33])[CH2:28][CH2:27]1)=O)(C)(C)C>C(O)C>[CH3:15][C:11]1([CH3:16])[CH2:10][CH2:9][C:8]([CH3:18])([CH3:17])[C:7]2[CH:6]=[C:5]([C:3]3[N:33]=[C:32]([CH:29]4[CH2:30][CH2:31][NH:26][CH2:27][CH2:28]4)[S:34][CH:2]=3)[CH:14]=[CH:13][C:12]1=2

Participants

4

Reactant 2

HCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 28013372-Bromo-1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one

Product 1

HCID 582464614-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.12 g (12.28 mmol) of 2-bromo-1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone and 3 g (12.28 mmol) of 4-thiocarbamoylpiperidine-1-carboxylic acid tert-butyl ester were suspended in 50 ml of ethanol and refluxed overnight. The reaction mixture was cooled and evaporated. The residue was slurried using a little EA and PE, digested and filtered off with suction. The solid was suspended in 180 ml of EA, washed with 60 ml of a saturated sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate, filtered and evaporated.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. filtrationfiltered off with suction
  5. washwashed with 60 ml of a saturated sodium hydrogencarbonate solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-91233daecc434ed0a6e7033d6d8cfde8
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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