Diethyl Ether → 1-(Benzyloxycarbonyl)-4-[(4-nitrophenoxy)methyl]piperidine

HRID 345445Notes

Reaction equation

HRID 345445 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][OH:20])[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1.CCOCC>O1CCCC1>[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][O:20][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 199924221-(Benzyloxycarbonyl)-4-[(4-nitrophenoxy)methyl]piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (3.36 g of a 50% dispersion in mineral oil) was added portionwise to a stirred solution of the product of part (i) (17.43 g) in dry tetrahydrofuran (200 ml) and the mixture was stirred at room temperature for 1 hour. 4-Fluoronitrobenzene (9.87 g) was added dropwise and the mixture was stirred for a further 18 hours and then evaporated. Water was added to the residue and the mixture was extracted several times with dichloromethane. The combined extracts were washed with water, dried (MgSO4) and evaporated to give an oil which solidified on trituration with ether. The solid was filtered off, washed with a little ether and crystallised from ethyl acetate/hexane to give the product, (13.51 g), m.p. 121°-122°.

Workup

  1. stirringthe mixture was stirred for a further 18 hours
  2. customevaporated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted several times with dichloromethane
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. filtrationThe solid was filtered off
  10. washwashed with a little ether
  11. customcrystallised from ethyl acetate/hexane
  12. customto give the product, (13.51 g), m.p. 121°-122°

Sources & evidence

ORD record
ord-28fb6a3c823842c39ae274e0264e68e3
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

Loading…