HCID 1712173, compound → 1-[4-(Heptyloxy)phenyl]methanamine

HRID 324103Notes

Reaction equation

HRID 324103 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=O)=[CH:17][CH:16]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>C1COCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][NH2:21])=[CH:22][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 1712173HCID 1712173, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 151155341-[4-(Heptyloxy)phenyl]methanamineYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (1.928 g, 52.23 mmol) in THF (150 ml) at room temperature under nitrogen was added a suspension of 4-(heptyloxy)benzamide (6.146 g, 26.117 mmol). After refluxing for 22 h, reaction was cooled in an ice bath and quenched in the following order: water (2.09 ml), 15% NaOH (2.09 ml) and water (6.26 ml). The mixture was stirred for 3 h followed by the addition of Na2SO4. The mixture was filtered and concentrated in vac. The residue was taken up in Et2O, filtered, concentrated, and the resulting residue taken up in hexane, filtered, concentrated, and dried to give the desired product as a hazy yellow oil (4.872 g, 84%): 1H NMR (400 MHz, DMSO-d6) δ0.86 (t, J=7 Hz, 3H), 1.22-1.42 (m, 8H), 1.64-1.72 (m, 2H), 1.82 (broad s, 2H), 3.13 (s, 2H), 3.89 (t, J=6.6 Hz, 2H), 6.80-6.84 (m, 2H), 7.17-7.21 (m, 2H); IR (film) 2940, 2850, 1510, 1250 cm−1; mass spectrum [(+)ESI], m/z 222 (M+H)+.

Workup

  1. additionwas added
  2. temperatureAfter refluxing for 22 h
  3. customreaction
  4. temperaturewas cooled in an ice bath
  5. customquenched in the following order
  6. additionfollowed by the addition of Na2SO4
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated in vac
  9. filtrationfiltered
  10. concentrationconcentrated
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customdried

Sources & evidence

ORD record
ord-d321d85ec89e4b3e90543c55a32e2fae
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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