Trifluoroacetic acid → [3-(Benzo[b]thiophen-4-yloxy)-4-cyclohexyl-butyl]-methyl-amine

HRID 2220359Notes

Reaction equation

HRID 2220359 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([CH2:16][CH2:17][CH:18]([O:26][C:27]1[C:35]2[CH:34]=[CH:33][S:32][C:31]=2[CH:30]=[CH:29][CH:28]=1)[CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)C)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[S:32]1[CH:33]=[CH:34][C:35]2[C:27]([O:26][CH:18]([CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:17][CH2:16][NH:14][CH3:13])=[CH:28][CH:29]=[CH:30][C:31]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58591173[3-(Benzo[b]thiophen-4-yloxy)-4-cyclohexyl-butyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 10041545[3-(Benzo[b]thiophen-4-yloxy)-4-cyclohexyl-butyl]-methyl-amineYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add trifluoroacetic acid (5.5 ml, 71 mmol) to a stirred solution of [3-(benzo[b]thiophen-4-yloxy)-4-cyclohexyl-butyl]-methyl-carbamic acid tert-butyl ester (1.49 g, 3.6 mmol) and dichloromethane (80 ml) at 0° C. under N2. Stir for 5 minutes at 0° C. and allow the reaction to reach room temperature. Stir for 90 minutes, add sodium bicarbonate. Partition between sodium bicarbonate and dichloromethane, wash the combined dichloromethane layers with brine, dry over sodium sulfate. Filter and concentrate to give the crude compound. Purify the compound by flash chromatography, eluting with 3% ethanol/0.3% ammonium hydroxide/chloroform to yield 0.511 g (45%) of the title compound: mass spectrum (ion spray) m/z=318 (M+1); HPLC (90/5/5 to 0/95/5 water/acetonitrile/5% formic acid) Xterra MS C18 2.1 mm×50 mm×3.5micron: Retention time 3.08 minutes, Purity 100%.

Workup

  1. customthe reaction
  2. customto reach room temperature
  3. stirringStir for 90 minutes
  4. customPartition between sodium bicarbonate and dichloromethane
  5. washwash the combined dichloromethane layers with brine
  6. dry with materialdry over sodium sulfate
  7. filtrationFilter
  8. concentrationconcentrate
  9. customto give the crude compound
  10. customPurify the compound by flash chromatography
  11. washeluting with 3% ethanol/0.3% ammonium hydroxide/chloroform

Sources & evidence

ORD record
ord-b5d36e666d5b448c8aaf96f6130dfa18
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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