Carbon Dioxide → HCID 23045627, compound

HRID 2108200Notes

Reaction equation

HRID 2108200 reaction equation
[CH2:1]([N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)=O.B(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+].[ClH:33]>C(Cl)Cl>[ClH:33].[CH2:1]([N:6]1[CH2:11][CH2:10][CH2:9][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 12937943HCID 12937943, compound

Product 1

HCID 23045627HCID 23045627, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-pentyl-3-(3-methoxyphenyl)piperidine (1.3 g, 0.005 mol) in CH2Cl2 (20 ml) was cooled with dry ice and BBr3 (1.6 g, 0.006 mol) was added dropwise. The mixture was then held at -78° C. for 1 h and then allowed to reach r.t. overnight. The solution was made alkaline with aqueous Na2CO3, extracted with CH2Cl2 and the organic phase dried with Na2SO4. Evaporation of the solvent afforded an oily residue which was treated with HCl-saturated ethanol (5 ml). After evaporation of solvent, purification by extractions and recrystallization (ethanol/ether), the desired product (0.40 g, 29%) was obtained, mp. 70°-80° C.

Workup

  1. additionwas added dropwise
  2. waitto reach r.t. overnight
  3. extractionextracted with CH2Cl2
  4. dry with materialthe organic phase dried with Na2SO4
  5. customEvaporation of the solvent
  6. customafforded an oily residue which
  7. customAfter evaporation of solvent, purification
  8. extractionby extractions and recrystallization (ethanol/ether)

Sources & evidence

ORD record
ord-93f1de0079bc448c887378a82174f37a
Source dataset
uspto-grants-1990_06
Patent number
US04937346

Reaction notes

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