Trifluoroacetic acid → HCID 67247410, compound

HRID 2273182Notes

Reaction equation

HRID 2273182 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH:21]2[CH2:34][C:33]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:35][CH3:36])[CH:31]=4)[N:26]=[CH:25][C:24]=3[O:23][CH2:22]2)[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[CH3:36][O:35][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][C:24]1[O:23][CH2:22][CH:21]([N:18]3[CH2:17][CH2:16][CH:15]([NH2:14])[CH2:20][CH2:19]3)[CH2:34][C:33]2=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67246989HCID 67246989, compound

Product 1

HCID 67247410HCID 67247410, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.23 mL, 15.78 mmol, 15.0 eq) is added at 0° C. to a stirred solution of [1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene-3-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (500 mg, 1.05 mmol, 1.0 eq) in dichloromethane (50 mL). After 15 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×30 mL) and water (30 mL) and the pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthrene-3-yl)-piperidin-4-ylamine as a brown solid (325 mg, 84% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×30 mL) and water (30 mL)
  2. additionthe pH is adjusted to 12 by the addition of a 1N sodium hydroxide aqueous solution
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d629403636b64d14a42b8395fe87ba49
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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