Triethylamine → HCID 55028620, compound

HRID 1191036Notes

Reaction equation

HRID 1191036 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1)#[N:9].[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21]>C(Cl)Cl>[CH3:18][C:19]([CH3:24])([CH3:23])[C:20]([NH:9][CH2:8][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 55028620HCID 55028620, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add triethylamine (0.3 mL, 2.12 mmol) to a solution of 4-cyano-benzylamine (1.0 g, 7.58 mmol) in DCM (11 mL) and cool the mixture at 0° C. Add 2,2-dimethyl-propionyl chloride (0.93 mL, 7.58 mmol) dropwise and allow to stir the mixture at 0° C. for 15 min and at room temperature for 2 h. Add water, separate the organic phase and extract the aqueous phase twice with DCM. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate (1.23 g, 75%).

Workup

  1. waitat room temperature for 2 h
  2. customAdd water, separate the organic phase
  3. extractionextract the aqueous phase twice with DCM
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-1c3972214abf46229b872de93660b556
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…