Putrescine → HCID 15728468, compound

HRID 1084915Notes

Reaction equation

HRID 1084915 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:8])[CH:5]=[CH:6][CH:7]=1.NCCCCN.C([Li])CCC.[Cl:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23].[Cl-].[NH4+]>CCOCC.CCCCCC>[Cl:20][C:21]([F:28])([F:27])[C:22]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[CH:3]=1)=[O:23]

Participants

8

Reactant 5

HCID 1045PutrescineHCID 79281-Bromo-3-chlorobenzeneHCID 25517Ammonium ChlorideHCID 67843Acetic acid, 2-chloro-2,2-difluoro-, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 15728468HCID 15728468, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8058HexaneSolvent

Procedure

A solution of 25 g of 3-bromochlorobenzene in 100 ml ether was added to a solution of 15.1 g of tetramethylenediamine, 52.4 ml of a 2.5M solution of n-butyllithium in hexane and 75 ml ether at -78° C. under nitrogen. After 1 hour, a solution of 31.0 g of ethyl chlorodifluoroacetate in 150 ml ether was added. After warming to room temperature, the reaction was poured into excess ammonium chloride solution and extracted with ether. The extracts were dried (Na2SO4) and evaporated. The residue was distilled (0.1 mm Hg) to give 14.7 g of an oil which was used directly.

Workup

  1. extractionextracted with ether
  2. dry with materialThe extracts were dried (Na2SO4)
  3. customevaporated
  4. distillationThe residue was distilled (0.1 mm Hg)

Sources & evidence

ORD record
ord-c2a0cf05097449d686c746e56af25384
Source dataset
uspto-grants-1991_04
Patent number
US05006563

Reaction notes

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