Diisopropylethylamine → HCID 69569966, compound

HRID 2219938Notes

Reaction equation

HRID 2219938 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:24][CH2:23][C:22]2[C:21]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:20][C:19]([NH2:36])=[CH:18][C:17]=2[CH2:16]1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C>ClCCCl>[F:35][C:32]([F:33])([F:34])[C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:21]2[C:22]3[CH2:23][CH2:24][NH:15][CH2:16][C:17]=3[CH:18]=[C:19]([NH2:36])[CH:20]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 69222715HCID 69222715, compound

Product 1

HCID 69569966HCID 69569966, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Chloroethyl chloroformate (864 mg, 6 mmol) was added dropwise to the solution of 2-benzyl-N5-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-5,7-diamine (1.2 g, 3 mmol) and diisopropylethyl amine (774 mg, 6 mmol) in 1,2-dichloroethane (30 mL, anhydrous) at 0° C. After addition, the reaction mixture was stirred at room temperature for 1 hr. Solvent was removed in vacuo, residue was dissolved in methanol (10 mL) and was stirred at room temperature for 10 h. Solvent was removed in vacuo and solid residue was washed by diethyl ether. Product was obtained as a light brown solid (834 mg, 90%).

Workup

  1. additionAfter addition
  2. customSolvent was removed in vacuo, residue
  3. dissolutionwas dissolved in methanol (10 mL)
  4. stirringwas stirred at room temperature for 10 h
  5. customSolvent was removed in vacuo and solid residue
  6. washwas washed by diethyl ether

Sources & evidence

ORD record
ord-bebe23f176ea489987177bc76ca45c1c
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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