Trifluoroacetic acid → 4-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidine

HRID 1108320Notes

Reaction equation

HRID 1108320 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][CH2:22][C:23]2[O:24][C:25]3[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[C:28]([Br:34])[C:26]=3[CH:27]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[Br:34][C:28]1[C:26]2[CH:27]=[C:23]([CH2:22][O:21][CH:18]3[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]3)[O:24][C:25]=2[C:31]([O:32][CH3:33])=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 540770204-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 187848694-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidineYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (5 ml) was added to a stirred solution of 4-(4-bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester (1.3 g) in dichloromethane (50 ml). After stirring at room temperate overnight the reaction was diluted with dichloromethane (150 ml) washed with 1M sodium hydroxide (100 ml) and dried over magnesium sulfate. The organic phase was concentrated in vacuo to afford the title compound as a pale yellow gum (0.98 g).

Workup

  1. washwashed with 1M sodium hydroxide (100 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-ce50eecc609e43c3b6455bd48d38dc13
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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