Dichloromethane → HCID 20689421, compound

HRID 447393Notes

Reaction equation

HRID 447393 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-b2a7f710bc204dbab595ae218a373ce8
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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