Triethylamine → HCID 12030671, compound

HRID 1591745Notes

Reaction equation

HRID 1591745 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl.[NH2:13][CH2:14][CH2:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH2:15][CH2:14][NH:13][C:2](=[O:3])[O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:17][CH:18]=1)#[N:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 457891874-(2-Aminoethyl)benzonitrile--hydrogen chloride (1/1)

Product 1

HCID 12030671HCID 12030671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

With ice bath cooling, 5.82 ml (15.57 mmol) of benzyl chloroformate (45% in toluene) were added to a solution of 2.37 g (12.98 mmol) of 4-(2-aminoethyl)benzonitrile hydrochloride and 4.34 ml (31.14 mmol) of triethylamine in 95 ml of dichloromethane. The reaction mixture was stirred at room temperature overnight and then evaporated to dryness. The crude product obtained in this manner was purified by column chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 2:1 to 1:1).

Workup

  1. temperatureWith ice bath cooling
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-146e0ebcbb3744069a9703bb0592e35a
Source dataset
uspto-grants-2007_11
Patent number
US07291642B2

Reaction notes

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