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 1168883Notes

Reaction equation

HRID 1168883 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-d2654817c256460fa13420422f246aaa
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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