6-Aminohexanoic Acid → Tert-butyl 6-aminohexanoate

HRID 2305253Notes

Reaction equation

HRID 2305253 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.C(=O)(O)[O-].[Na+].[CH3:19][C:20](O)([CH3:22])[CH3:21]>>[C:20]([O:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])([CH3:22])([CH3:21])[CH3:19]

Participants

5

Reactant 4

HCID 5646-Aminohexanoic AcidHCID 6386tert-ButanolHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 10750089Tert-butyl 6-aminohexanoateYield 53%

Conditions

Temperature
25 °C

Procedure

In a 10 L reaction flask equipped with N2 inlet, 0.383 Kg of 6-aminocaproic acid (2.92 mol) was slowly added to 3.14 Kg of stirring thionyl chloride (26.28 mol). The maximum temperature during the addition is kept at about 30° C. Upon complete addition, the reaction was allowed to stir at 20-30° C. for 1 h, then concentrated via rotary evaporation (max 40° C. bath). Excess thionyl chloride was chased-off by the addition of toluene (0.843 Kg) and the solution was re-concentrated via rotary evaporation (max 40° C. bath). To the resulting tan solid a suspension of 0.537 Kg of sodium bicarbonate (6.42 mol) was added in 2.97 Kg of t-BuOH (40.3 mol) and reaction allowed to stir at 20-30° C. for 2 h. The excess t-BuOH was removed in vacuo (max 40° C. bath) and residue diluted with 5.17 Kg of ethyl acetate and washed with four portions of 1M NaOH (0.307 Kg in 7.68 Kg water), three portions of H2O (1.92 Kg), one portion of sat. aq. NaCl (0.767 Kg in 1.92 Kg water), dried with anhydrous Na2SO4 (0.383 Kg), filtered via Buchner funnel, rinced with ethyl acetate (1.72 Kg), and concentrated in vacuo (max 50° C. bath). The tan liquid residue was distilled (bp 97-98° C./2 mmHg) to afford 0.290 Kg of t-butyl-6-aminocaproate (53% yld) as a clear colourless to light yellow oil.

Workup

  1. customIn a 10 L reaction flask
  2. customequipped with N2 inlet
  3. additionThe maximum temperature during the addition
  4. customis kept at about 30° C
  5. additionUpon complete addition
  6. concentrationconcentrated via rotary evaporation (max 40° C. bath)
  7. additionExcess thionyl chloride was chased-off by the addition of toluene (0.843 Kg)
  8. concentrationthe solution was re-concentrated via rotary evaporation (max 40° C. bath)
  9. customreaction
  10. stirringto stir at 20-30° C. for 2 h
  11. customThe excess t-BuOH was removed in vacuo (max 40° C. bath) and residue
  12. additiondiluted with 5.17 Kg of ethyl acetate
  13. washwashed with four portions of 1M NaOH (0.307 Kg in 7.68 Kg water), three portions of H2O (1.92 Kg), one portion of sat. aq. NaCl (0.767 Kg in 1.92 Kg water)
  14. dry with materialdried with anhydrous Na2SO4 (0.383 Kg)
  15. filtrationfiltered via Buchner funnel
  16. concentrationconcentrated in vacuo (max 50° C. bath)
  17. distillationThe tan liquid residue was distilled (bp 97-98° C./2 mmHg)

Sources & evidence

ORD record
ord-5bdfde2d831443bca20c84f213695033
Source dataset
uspto-grants-2002_08
Patent number
US06440417B1

Reaction notes

Loading…