Isobutyric Acid → HCID 18469925, compound

HRID 2228469Notes

Reaction equation

HRID 2228469 reaction equation
[CH:1]1([N:11]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:18](O)(=O)[CH:19]([CH3:21])[CH3:20].[BH4-].[Na+].[OH-].[Na+]>O>[CH:1]1([N:11]2[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6590Isobutyric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 11287680HCID 11287680, compound

Product 1

HCID 18469925HCID 18469925, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 mL flask was charged with R 1-(1,2,3,4-tetrahydronaphthyl)-homopiperazine (1.12 g, 4.85 mmol) and isobutyric acid (12.8 g, 145 mmol). The flask was immersed in a 50° C. oil bath. After heating for 10 minutes, NaBH4 was added in portions over 15 minutes. After heating for 16 hours, the resulting mixture was immersed in an ice water bath and water (20 mL) was added. NaOH pellets were added until the solution was strongly basic. The mixture was then extracted with ethyl acetate (3×125 mL) and the combined extracts were dried over anhydrous MgSO4, filtered and concentrated to give a yellow oil. This crude product was purified by simple distillation under reduced pressure using a short-path distillation apparatus (bp=121-126° C., 120 mtorr) to obtain the title compound as a colorless oil (1.19 g). 1H NMR (CDCl3, 300 MHz) δ 0.89 (d, 6H), 1.58-1.76 (m, 5H), 1.93-2.08 (m, 2H), 2.24 (d, 2H), 2.59-2.77 (m, 10H), 3.86 (m, 1H), 7.02-7.18 (m, 3H). 777 (d, 1H); m/s: M+H+ 287.

Workup

  1. customwas immersed in a 50° C.
  2. temperatureAfter heating for 10 minutes
  3. temperatureAfter heating for 16 hours
  4. customthe resulting mixture was immersed in an ice water bath
  5. extractionThe mixture was then extracted with ethyl acetate (3×125 mL)
  6. dry with materialthe combined extracts were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a yellow oil
  10. distillationThis crude product was purified by simple distillation under reduced pressure

Sources & evidence

ORD record
ord-0561cf1133c64ff6a4a6846bbb4082f7
Source dataset
uspto-grants-2002_07
Patent number
US06417183B1

Reaction notes

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