Hydrochloric Acid → HCID 18971623, compound

HRID 2395263Notes

Reaction equation

HRID 2395263 reaction equation
[Cl:1][CH2:2][CH2:3][C:4](Cl)=[O:5].N1CCCCC1.[Br-:13].[NH2:14][C:15]1[CH:40]=[CH:39][CH:38]=[CH:37][C:16]=1[CH2:17][P+:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl>[Br-:13].[Cl:1][CH2:2][CH2:3][C:4]([NH:14][C:15]1[CH:40]=[CH:39][CH:38]=[CH:37][C:16]=1[CH2:17][P+:18]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 693643-Chloropropionyl chlorideHCID 10961315(2-Aminobenzyl)triphenylphosphonium bromide

Product 1

HCID 18971623HCID 18971623, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chioropropionyl chloride (3.0 ml, 32 mmol) and piperidine (3.5 ml, 43.5 mmol) were added to a suspension of 2-aminobenzyltriphenylphosphonium bromide (13.0 g, 29 mmol) (synthesised using the procedure of Capuano et al, Chem. Ber., 1986, 119, 2069-2074) in dichloromethane (60 ml) under a nitrogen atmosphere. The mixture was heated at reflux for 30 min. and then cooled to room temperature. Dichloromethane (60 ml) and hydrochloric acid (1N, 50 ml) were added and the precipitated solid was collected by filtration, washed with dichloromethane and dried in vacuo to give 2-(3-chloropropionylamino)benzyltriphenylphosphonium bromide (7.5 g, 48%). The filtrate was diluted with dichloromethane (300 ml) and washed with sodium carbonate (satd., 150 ml). Evaporation of the dichloromethane gave a residue which was triturated with ether (200 ml) and the white solid collected to afford a second crop of product (5.0 g, 32%).

Workup

  1. customsynthesised
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 30 min.
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with dichloromethane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8b8e5b349ef443379685193ec507f12d
Source dataset
uspto-grants-1998_09
Patent number
US05814644

Reaction notes

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