N-(7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2,2,2-trifluoro-N-propyl-acetamide → (7-Ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine

HRID 983477Notes

Reaction equation

HRID 983477 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([N:14]([CH2:21][CH2:22][CH3:23])C(=O)C(F)(F)F)[CH2:11]2)=[CH:6][CH:5]=1)[CH3:2]>CO.[OH-].[Na+]>[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH:14][CH2:21][CH2:22][CH3:23])[CH2:11]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 22560657N-(7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2,2,2-trifluoro-N-propyl-acetamide

Product 1

HCID 22560667(7-Ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-(7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2,2,2-trifluoro-N-propyl-acetamide (660 mg, 2.0 mmol) in methanol (30 mL) and 1 N NaOH (30 mL) was stirred at room temperature for 30 h. The reaction was concentrated and the residue partitioned between EtOAc (40 mL) and water (40 mL). The aqueous layer was extracted twice more with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4), and concentrated to afford (7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amine.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue partitioned between EtOAc (40 mL) and water (40 mL)
  3. extractionThe aqueous layer was extracted twice more with EtOAc (2×30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc09ac9f5ccf45f0b51b8ad2a587d02f
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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