Methyl Isobutyl Ketone → HCID 86720847, compound

HRID 2284882Notes

Reaction equation

HRID 2284882 reaction equation
[CH2:1]([CH2:6][O:7][CH2:8][CH2:9][NH2:10])[O:2][CH2:3][CH2:4][NH2:5].[CH3:11][CH:12]([CH3:17])[CH2:13][C:14](=O)[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[CH2:6]([O:7][CH2:8][CH2:9][NH:10][CH:14]([CH2:13][CH:12]([CH3:17])[CH3:11])[CH3:15])[CH2:1][O:2][CH2:3][CH2:4][NH:5][CH:14]([CH2:13][CH:12]([CH3:17])[CH3:11])[CH3:15]

Participants

6

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 70248Bis-Aminoethylglycol

Product 1

HCID 86720847HCID 86720847, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A 1 liter 3 necked round bottomed flask fitted with condenser, mechanical stirrer, dropping funnel, thermocouple and nitrogen inlet at <20 mL/min was charged with 20 g (0.1350 mol) of 2,2′-(ethylenedioxy)bis(ethylamine) in 450 mL of dichloromethane. STAB (31.44 g) was added with stirring. 31.0 g of 4-methyl-2-pentanone was then added drop-wise to the suspension over 40 mins. After cooling to 23° C. with an ice bath the mixture was stirred at room temperature for about 1.5 hours and left standing for a further day. The crude product was stirred with a mixture of saturated aqueous sodium carbonate solution (30%) (120 ml) and water (60 ml). The aqueous phase was diluted with water (100 ml), shaken, separated and washed with DCM (50 ml). The combined organic phase was washed with water (2×150 ml). It was then dried by shaking with magnesium sulphate and filtered.

Workup

  1. additionSTAB (31.44 g) was added
  2. stirringwas stirred at room temperature for about 1.5 hours
  3. waitleft
  4. waitstanding for a further day
  5. stirringshaken
  6. customseparated
  7. washwashed with DCM (50 ml)
  8. washThe combined organic phase was washed with water (2×150 ml)
  9. customIt was then dried
  10. stirringby shaking with magnesium sulphate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-e85b399747254136837a580d699c95d7
Source dataset
uspto-grants-2015_09
Patent number
US09145530B2

Reaction notes

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