Triphenylphosphine → HCID 54093094, compound

HRID 1252234Notes

Reaction equation

HRID 1252234 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][C:15](=[CH:18][CH2:19]O)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:42]N1C(=O)CCC1=O>O1CCCC1>[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:17][CH2:16][C:15](=[CH:18][CH2:19][Br:42])[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 53726542HCID 53726542, compound

Product 1

HCID 54093094HCID 54093094, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(1-p-nitrobenzyloxycarbonyl-4-piperidinylidene)ethyl alcohol (1.13 g) and triphenyl phosphine (1.94 g) in tetrahydrofuran (65 ml) was added N-bromosuccinimide (1.31 g) at room temperature and stirred for 2 hours. The reaction mixture was filtered to remove any insoluble materials and the filtrate was concentrated in vacuo to give an oily residue which was purified by silica gel chromatography to give 2-(1-p-nitrobenzyloxycarbonyl-4-piperidinylidene)ethylbromide.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove any insoluble materials
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give an oily residue which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-06dd7bab32af4cd98595eac40a23b3eb
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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