Triethylamine → HCID 22648420, compound

HRID 394003Notes

Reaction equation

HRID 394003 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7]C2CCCN2)=[C:4]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH2:16])[CH:3]=1.C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.Cl[P:31]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(OC)(C)C.C1CCCCC1.C(NC(C)C)(C)C>C1(C)C=CC=CC=1>[C:38]1([P:31]([CH:28]2[CH2:29][CH2:27][CH2:26][N:25]2[CH2:7][O:6][C:5]2[CH:13]=[CH:14][C:2]([CH3:1])=[CH:3][C:4]=2[C:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH2:16])[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66180ChlorodiphenylphosphineHCID 22648423HCID 22648423, compoundHCID 86591154HCID 86591154, compound

Product 1

HCID 22648420HCID 22648420, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 1.31 g (4.5 mmole)2-[4-methyl-2-(1-phenyl-vinyl)-phenoxymethyl]-pyrrolidine and 1.13 g (11.2 mmole) triethylamine in 12 ml abs. toluene at 0° within 30 minutes 1.00 g (4.6 mmole) P-chlorodiphenylphosphine in 3 ml abs. toluene are added dropwise. The reaction solution is left under agitation at RT for 20 h. Then the resultant triethylammonium chloride is filtered off, the residue is recleaned with 20 ml toluene and the filtrate is reduced on the rotary evaporator. Cleaning of the raw product obtained takes place by column chromatography on silica gel with MTBE/cyclohexane/diisopropylamine (ratio of volumes=5/1+10 Vol−%) as the eluant. 1.31 g (2.7 mmole, 61%)diphenylphosphanyl-[4-methyl-2-(1-phenyl-vinyl)-phenoxymethyl]-pyrrolidine are obtained.

Workup

  1. filtrationThen the resultant triethylammonium chloride is filtered off
  2. customthe filtrate is reduced on the rotary evaporator
  3. customCleaning of the raw product obtained

Sources & evidence

ORD record
ord-d7ecac4fe6ca4620a9cdd0a56c522f8a
Source dataset
uspto-grants-2004_10
Patent number
US06809225B2

Reaction notes

Loading…