2-Chloroethyl chloroformate → HCID 11647065, compound

HRID 251875Notes

Reaction equation

HRID 251875 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH:13]1[CH2:15][CH2:14]1)[CH2:6][C@H:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22].Cl[C:24]([O:26][CH2:27][CH2:28]Cl)=[O:25]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH:13]1[CH2:15][CH2:14]1)[CH2:6][C@H:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1[CH2:28][CH2:27][O:26][C:24]1=[O:25]

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 59682881HCID 59682881, compound

Product 1

HCID 11647065HCID 11647065, compoundYield 132.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-((R)-6,8-Dichloro-2-cyclopropyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (400 mg) was dissolved in absolute THF (25 ml), and 2-chloroethyl chloroformate (102 mg) was added with stirring. After stirring at room temperature for 3 h, the mixture was left to stand overnight. The solvent was then removed and the residue purified by means of preparative HPLC. The fractions comprising product were combined, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. After the combined ethyl acetate phases had been dried over magnesium sulfate, they were filtered and concentrated to dryness. 380 mg of the desired product were obtained.

Workup

  1. stirringAfter stirring at room temperature for 3 h
  2. waitthe mixture was left
  3. customThe solvent was then removed
  4. customthe residue purified by means of preparative HPLC
  5. customthe acetonitrile was removed on a rotary evaporator
  6. extractionextracted three times with ethyl acetate
  7. dry with materialAfter the combined ethyl acetate phases had been dried over magnesium sulfate, they
  8. filtrationwere filtered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-03689ddbef0448e79cdfb55cd1ec4d93
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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