Triethylamine → HCID 57342162, compound

HRID 901070Notes

Reaction equation

HRID 901070 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7]C(CCN)=[CH:5][CH:4]=1)#[N:2].C([N:14]([CH2:17][CH3:18])[CH2:15]C)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:18]([CH2:17][N:14]([CH3:15])[C:20](=[O:21])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 219125254-(2-Aminoethyl)benzonitrile

Product 1

HCID 57342162HCID 57342162, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 7 g (47.9 mM) of [(4-cyanophenyl)methyl]methanamine is prepared in 60 ml of DCM and 5.8 g (57.5 mM) of triethylamine are added. The mixture is cooled to 0° C. and a solution of 9.8 g (57.5 mM) of benzyl chloroformate in 20 ml of DCM is added dropwise. The mixture is then agitated for 20 hours at ambient temperature and then washed with a solution of 0.1 N hydrochloric acid, and then with water, dried over sodium sulphate and concentrated under reduced pressure. The residue is purified by chromatography on silica gel in eluting with the aid of a mixture of toluene/ethyl acetate (95/5; v/v). 11.4 g of the desired product are thus obtained as an oil (yield=87%).

Workup

  1. washwashed with a solution of 0.1 N hydrochloric acid
  2. dry with materialwith water, dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography on silica gel
  5. washin eluting with the aid of a mixture of toluene/ethyl acetate (95/5; v/v)

Sources & evidence

ORD record
ord-962d3326683544b1b14bf5b45b4885f8
Source dataset
uspto-grants-2008_04
Patent number
US07361687B2

Reaction notes

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