Propionic Acid → HCID 12741429, compound

HRID 1262863Notes

Reaction equation

HRID 1262863 reaction equation
[BH4-].[Na+].[C:3](O)(=O)[CH2:4][CH3:5].[H][H].[CH2:10]([NH:13][CH:14]1[CH2:23][CH:22]=[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH2:20]2)[CH2:15]1)[CH2:11][CH3:12].[OH-].[Na+]>C1C=CC=CC=1>[CH2:10]([N:13]([CH:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:24][CH3:25])[CH:20]=2)[CH2:15]1)[CH2:3][CH2:4][CH3:5])[CH2:11][CH3:12]

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 20456202HCID 20456202, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12741429HCID 12741429, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Sodium borohydride (26.85 g, 0.71 mol) was added in small portions to propionic acid (172.2 mL, 2.3 moles) in dry benzene (650 mL), maintaining the temperature below 20° C. When hydrogen evolution ceased, a solution of N-propyl-6-methoxy-1,2,3,5-tetrahydro-2-naphthylamine (30.93 g, 0.141 mol) in benzene (150 mL) was added and the resulting mixture was refluxed for 3 hr. The cooled mixture was shaken with excess 10% (w/v) sodium hydroxide solution. The organic layer was separated, dried over MgSO4 and evaporated to give a brown oil of N,N-dipropyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine, NMR (CDCl3) δ 0.85 (t, 6H), 1.45 (m, 6H), 2.45 (t, 4H), 2.7 (m, 5H), 3.70 (s, 3H) and 6.7 (m, 3H).

Workup

  1. temperaturemaintaining the temperature below 20° C
  2. temperaturethe resulting mixture was refluxed for 3 hr
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-80cd9beadba045a6b20aea2189d45f94
Source dataset
uspto-grants-1984_06
Patent number
US04454150

Reaction notes

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