Trifluoroacetic acid → 1-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-piperidin-4-ylamine

HRID 633817Notes

Reaction equation

HRID 633817 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]2[CH2:35][C:34]3[C:33]4[C:28](=[CH:29][CH:30]=[C:31]([O:36][CH3:37])[CH:32]=4)[N:27]=[CH:26][C:25]=3[O:24][CH2:23]2)[CH2:17][CH2:16]1)(C)(C)C>ClCCl>[CH3:37][O:36][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][C:25]1[O:24][CH2:23][CH:22]([CH2:21][N:18]3[CH2:19][CH2:20][CH:15]([NH2:14])[CH2:16][CH2:17]3)[CH2:35][C:34]2=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 711180001-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-piperidin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 867307021-(6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-piperidin-4-ylamineYield 114.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.25 mL, 16.10 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-phenanthren-3-ylmethyl)-piperidin-4-yl-carbamic acid tert-butyl ester (540 mg, 1.07 mmol, 1.0 eq) in dichloromethane (15 mL). After 2 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and water (20 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-phenanthren-3-ylmethyl)-piperidin-4-ylamine as an orange viscous oil (400 mg, 97% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL) and water (20 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-f7f6ac7f1ed3452ca1736174c25bf5b7
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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