Water → HCID 13656123, compound

HRID 746051Notes

Reaction equation

HRID 746051 reaction equation
[C:1]1([C:7]2([CH2:16][CH2:17][CH2:18][N:19](C)[CH3:20])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30].O>C(Cl)Cl>[C:1]1([C:7]2([CH2:16][CH2:17][CH2:18][N:19]([C:29]([O:31][CH2:32][C:33]([Cl:36])([Cl:35])[Cl:34])=[O:30])[CH3:20])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 13656122HCID 13656122, compound

Product 1

HCID 13656123HCID 13656123, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-(3-phenyl-2,3-dihydrobenzofuran-3-yl)-N,N-dimethylpropylamine (7.40 g, 26 mmol), anhydrous K2CO3 (14.3 g, 104 mmol), and CH2Cl2 (125 ml) was stirred at 5°. A solution of 2,2,2-trichloroethyl chloroformate (4.3 ml, 32 mmol) in CH2Cl2 (5 ml) was added dropwise over 15 minutes. The reaction mixture was stirred at room temperature for 4 hours. Water was then added to dissolve the inorganic salts and the phases were separated. The organic phase was washed with saturated NaHCO3 and saturated NaCl, dried over Na2SO4, filtered, and evaporated in vacuo to give 7.6 g of a crude oil. This residue was chromatographed by HPLC using CH2Cl2 /hexane (2:1, by volume) as an eluent to yield 3.5 g (30%) of an oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 4 hours
  2. dissolutionto dissolve the inorganic salts
  3. customthe phases were separated
  4. washThe organic phase was washed with saturated NaHCO3 and saturated NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give 7.6 g of a crude oil
  9. customThis residue was chromatographed by HPLC

Sources & evidence

ORD record
ord-c1f021747d4f4031860f0b6392e9fc73
Source dataset
uspto-grants-1986_07
Patent number
US04602035

Reaction notes

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