6-Aminohexanoic Acid → HCID 437326, compound

HRID 979740Notes

Reaction equation

HRID 979740 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[C:12](Cl)(=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O>CCOCC>[C:12]([NH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 5646-Aminohexanoic AcidHCID 962WaterHCID 8166Dodecanoyl chloride3×HCID 14798Sodium Hydroxide2×

Product 1

HCID 437326HCID 437326, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A one L beaker was charged with 250 mL of 1N sodium hydroxide solution (0.25 mol) and 32.8 g (0.25 mol) of 6-aminocaproic acid. The resulting solution was cooled in an ice bath and, with stirring, a solution of lauroyl chloride (54.7 g, 0.25 mol) in 100 mL ether was added dropwise while maintaining the pH of the stirred solution between 10 and 12 by addition of 10% sodium hydroxide solution. Addition of the lauroyl chloride required 45 min. During this period the reaction mixture became thick with solid and additional volumes of water and ether were added in order to keep the mixture stirrable. Following completion of the lauroyl chloride addition, the ice bath was removed and the mixture was stirred for 1.5 hr. at room temperature. The mixture was then adjusted to pH 2 with concentrated HCl, and the precipitate which formed was removed by filtration and washed with water. The resulting solid was slurried with hexane (200 ml), filtered, and washed 5 times with 100 ml portions of hexane. This hexane slurry/wash procedure was repeated a second time. The resulting solid was air dried to yield 70.7 g (90%) of N-lauroyl-6-aminocaproic acid, mp 87°-90° C. [lit mp 85°-86° C.--E. Jungerman, J. F. Gerecht, and I. J. Krems, J. Amer. Chem. Soc., 78, 172 (1956).]

Workup

  1. temperatureThe resulting solution was cooled in an ice bath
  2. temperaturewhile maintaining the pH of the stirred solution between 10 and 12
  3. additionwere added in order
  4. customthe ice bath was removed
  5. stirringthe mixture was stirred for 1.5 hr
  6. customat room temperature
  7. customthe precipitate which formed
  8. customwas removed by filtration
  9. washwashed with water
  10. filtrationfiltered
  11. washwashed 5 times with 100 ml portions of hexane
  12. washThis hexane slurry/wash procedure
  13. customdried

Sources & evidence

ORD record
ord-16d1368446524b599b8fd03e8f42d4b8
Source dataset
uspto-grants-1987_01
Patent number
US04634551

Reaction notes

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