Tetrahydrofuran → (1-Benzyl-4-piperidyl)methanamine

HRID 1821743Notes

Reaction equation

HRID 1821743 reaction equation
[CH2:1]([NH:8][C:9](=O)[CH:10]1[CH2:15][CH2:14][NH:13]CC1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:23]1COC[CH2:24]1>>[NH2:13][CH2:14][CH:15]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 3868064N-benzylpiperidine-4-carboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514444(1-Benzyl-4-piperidyl)methanamine

Procedure

To a solution of N-benzylisonipecotamide (7.34 g, 34 mmol) in 60 mL of anhydrous THF, was added, LiAlH4 (1.9 g, 51 mmol) and the mixture was stirred at room temperature for 10 minutes followed by heating to reflux for 3 h. The reaction was quenched by addition of 100 mL sat'd. sodium potassium tartrate, and was extracted with EtOAc (3×50 mL). The combined extracts were washed with 20 mL water and 20 mL brine then dried over MgSO4, filtered and concentrated to give the desired product. 1H-NMR (400 MHz, CDCl3) δ 7-13 (m, 5H), 3.42 (s, 2H), 2.91 (m, 2H), 2.59 (m, 2H), 1.97 (m, 2H), 1.62 (m, 2H), 2.21 (m, 5H).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 3 h
  3. customThe reaction was quenched by addition of 100 mL
  4. extractionsodium potassium tartrate, and was extracted with EtOAc (3×50 mL)
  5. washThe combined extracts were washed with 20 mL water and 20 mL brine
  6. dry with materialthen dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-42a4dd0e0fa347d68a38ecc94efd04ac
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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