Water → HCID 10639134, compound

HRID 2400561Notes

Reaction equation

HRID 2400561 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.Br[CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.O>CN(C=O)C>[C:8]([C:7]1[CH:10]=[CH:11][C:4]([O:3][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]2)=[CH:5][CH:6]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 10639134HCID 10639134, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil; 316 mg, 7.91 mmol) in DMF (10 mL) was added in portions 4-hydroxybenzonitrile (856 mg, 7.19 mmol). After stirring for 15 min at rt, tert-butyl 4-(bromomethyl)piperidine-1-carboxylate (2.00 g, 7.19 mmol) was added, and the reaction mixture was stirred at 80° C. for 1 h and at 150° C. for a further 1 h. After cooling to rt, water was added, and the mixture was stirred for 15 min. The solid was filtered off, water was added again, and the mixture was stirred for further 15 min and then filtered again. This procedure was repeated once again. Finally, the solids obtained were dried in vacuo to give the title compound (1.47 g, 59%): ES-MS m/z 317, HPLC RT (Method F) 2.54 min.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 1 h and at 150° C. for a further 1 h
  2. temperatureAfter cooling to rt
  3. stirringthe mixture was stirred for 15 min
  4. filtrationThe solid was filtered off
  5. additionwater was added again
  6. stirringthe mixture was stirred for further 15 min
  7. filtrationfiltered again
  8. customFinally, the solids obtained
  9. customwere dried in vacuo

Sources & evidence

ORD record
ord-f3dfffbafd1643e9975b89ac3706ebc2
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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