Neopentylamine → (+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrile

HRID 1191047Notes

Reaction equation

HRID 1191047 reaction equation
C[Al](C)C.[CH3:5][C:6]([CH3:10])([CH3:9])[CH2:7][NH2:8].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:25])[C:20](OCC)=[O:21])=[CH:15][CH:14]=1)#[N:12]>C(Cl)Cl>[CH3:5][C:6]([CH3:10])([CH3:9])[CH2:7][NH:8][C:20]([CH:19]([C:16]1[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:18][CH:17]=1)[CH3:25])=[O:21]

Participants

5

Reactant 3

HCID 79882NeopentylamineHCID 4550989Ethyl 2-(4-cyanophenyl)propanoateHCID 16682925Trimethylaluminum

Product 1

HCID 58495675(+/-)-4-[1-(2,2-Dimethylpropyl-carbamoyl)-ethyl]-benzonitrileYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add AlMe3 (1.72 mL, 3.44 mmol, 2M solution in hexane) to a solution of 2,2-dimethyl-propylamine (402 μL, 3.44 mmol) in DCM (0.5 mL) under nitrogen atmosphere. Stir the mixture for 15 min at room temperature and add ethyl 2-(4-cyanophenyl)propanoate. Heat the mixture at 40° C. overnight. Quench the reaction with 10N aqueous HCl and extract twice with DCM. Dry the combined organics extracts over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (7:3) to obtain the desired intermediate (170 mg, 41%).

Workup

  1. temperatureHeat the mixture at 40° C. overnight
  2. customQuench
  3. customthe reaction with 10N aqueous HCl
  4. extractionextract twice with DCM
  5. customDry the combined
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (7:3)

Sources & evidence

ORD record
ord-0350be10c0104e4fbe5b6b13766b71a5
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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