Diethyl Ether → 1-(4-Chlorobenzyl)-2,2-dimethyl-propylideneamine hydrochloride

HRID 605583Notes

Reaction equation

HRID 605583 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(OCC)C.[Mg].[CH3:16][C:17]([CH3:21])([CH3:20])[C:18]#[N:19]>C1(C)C=CC=C(C)C=1>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:18](=[NH:19])[C:17]([CH3:21])([CH3:20])[CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 12416PivalonitrileHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5462224Magnesium

Product 1

HCID 865935051-(4-Chlorobenzyl)-2,2-dimethyl-propylideneamine hydrochloride

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

4-Chlorobenzyl bromide (0.1 mol) and dry diethyl ether (200 mL) are placed in a flame-dried, 2-necked round bottomed flask at RT. The solution is stirred under an inert atmosphere while magnesium turnings (0.1 mol) are added portionwise. Trimethylacetonitrile (0.1 mol) is then added, followed by dry m-xylene (100 mL). The reaction is stirred at RT for 1 h and then the diethyl ether is distilled off (oil bath temp. 130° C.). A further portion of trimethylacetonitrile (5 mL) is added and the resulting suspension is heated at reflux overnight under an atmosphere of dry nitrogen. The reaction mixture is cooled to 0° C. and a solution of concentrated hydrochloric acid (22 mL) in water (40 mL) is added slowly. The resulting solid is filtered off and dried under vacuum to give 1-(4-chlorobenzyl)-2,2-dimethyl-propylideneamine hydrochloride.

Workup

  1. customare placed in a flame-dried, 2-necked round bottomed flask at RT
  2. additionare added portionwise
  3. distillationthe diethyl ether is distilled off (oil bath temp. 130° C.)
  4. additionA further portion of trimethylacetonitrile (5 mL) is added
  5. temperaturethe resulting suspension is heated
  6. temperatureat reflux overnight under an atmosphere of dry nitrogen
  7. temperatureThe reaction mixture is cooled to 0° C.
  8. additiona solution of concentrated hydrochloric acid (22 mL) in water (40 mL) is added slowly
  9. filtrationThe resulting solid is filtered off
  10. customdried under vacuum

Sources & evidence

ORD record
ord-5423838df0094c1eae9a7ed1b16e4725
Source dataset
uspto-grants-2011_03
Patent number
US07915264B2

Reaction notes

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