Dichloromethane → HCID 20689421, compound

HRID 1466353Notes

Reaction equation

HRID 1466353 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 10760574Tert-butyl 4-(4-bromobenzyl)piperidine-1-carboxylate

Product 1

HCID 20689421HCID 20689421, compoundYield 93%

Procedure

To a solution of tert-butyl 4-(4-bromobenzyl)piperidine-1-carboxylate (780 mg, 2.2 mmol) in CH2Cl2 (15 mmol), was added TFA (0.5 mL) and the mixture was stirred at rt for 1 h. The solvent was removed in vacuo and the residue dissolved into CH2Cl2 (50 mL), washed with NaOH (0.1M, 10 mL), brine (10 mL), dried over MgSO4 and concentrated to dryness to give the title compound as a beige solid (520 mg, 93%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved into CH2Cl2 (50 mL)
  3. washwashed with NaOH (0.1M, 10 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-04b4e5e72c924f5eb0f20f37ef0699f1
Source dataset
uspto-grants-2015_04
Patent number
US08999968B2

Reaction notes

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