Triphenylphosphine → HCID 22264575, compound

HRID 915820Notes

Reaction equation

HRID 915820 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[O:14])[CH:9]([CH2:24][CH2:25]O)[CH2:8]2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:74]=[N+:75]=[N-:76])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][C:13]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:27]=[CH:28][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:8][CH:9]2[CH2:24][CH2:25][N:74]=[N+:75]=[N-:76])=[O:14])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11429681HCID 11429681, compound

Product 1

HCID 22264575HCID 22264575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-fluorobenzyl)-1-((4-chlorophenoxy)methyl)carbonyl-2-(2-hydroxyethyl)piperazine (0.134 g, 0.33 mmol) and triphenylphosphine (0.100 g) in THF (6 mL) at 0° C. was added diethyl azodicarboxylate (0.060 mL) and diphenylphosphoryl azide (0.081 mL). The mixture was stirred at ambient temperature for 2 days, then concentrated of volatiles in vacuo. Purification by flash column chromatography on silica gel afforded 0.047 g of 1-((4-chlorophenoxy)methyl)carbonyl-2-(2-azidoethyl)-4-(4-fluorobenzyl)piperazine as a clear, colorless oil; NMR (CDCl3) 7.3 (m, 4), 7.0 (t, 2), 6.9 (d, 2), 4.7 (m, 3), 4.4 (br d, 1), 4.3 (m, 1), 4.1 (m, 1), 3.5-3.1 (m, 4), 2.8 (d, 1), 2.7 (d, 1), 2.1 (m, 2), 1.8 (m, 1) ppm.

Workup

  1. concentrationconcentrated of volatiles in vacuo
  2. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-642cc5afb1e545cfa4ebeb0ecadabbdd
Source dataset
uspto-grants-2007_09
Patent number
US07268140B2

Reaction notes

Loading…