Trifluoroacetic acid → (7-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-yl-propyl-amine

HRID 393207Notes

Reaction equation

HRID 393207 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][C:22]([Br:28])=[CH:23][CH:24]=3)[CH2:19]2)[CH2:15][CH2:16][CH3:17])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:28][C:22]1[CH:21]=[C:20]2[C:25]([CH2:26][CH2:27][CH:18]([N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH2:15][CH2:16][CH3:17])[CH2:19]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11362947HCID 11362947, compound

Product 1

HCID 22649540(7-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-yl-propyl-amineYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (347 g, 0.77 mmol) in methylene chloride (30 mL) under a nitrogen atmosphere was added trifluoroacetic acid (10 mL). The reaction was stirred at room temperature for 30 min., and concentrated in vacuo. The residue was partitioned between EtOAc (50 mL) and 10% aq. KOH (50 mL). The organic layer was separated, dried over MgSO4, filtered, and concentrated to afford (7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-piperidin-4-yl-propyl-amine (203 mg).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc (50 mL) and 10% aq. KOH (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e7053776b1e4153b262d7992671f24d
Source dataset
uspto-grants-2004_10
Patent number
US06806278B2

Reaction notes

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