Ethanol → HCID 16785613, compound

HRID 661507Notes

Reaction equation

HRID 661507 reaction equation
ClC[CH:3]([OH:16])[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.[CH3:17][NH:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[CH2:25](O)C>>[NH2:5][CH2:4][CH:3]([OH:16])[CH2:17][N:18]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 7514N-MethylcyclohexylamineHCID 2621031-chloro-3-phthalimido-2-propanol

Product 1

HCID 16785613HCID 16785613, compoundYield 31%

Procedure

A mixture of 2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione 7.2 g (0.03 mol) (Weizmann, M. et al. Bull. soc. chim. 1930, 47:356-61) and N-methylcyclohexanamine 6.8 g (0.06 mol) in 25 ml ethanol was refluxed for 6 hours, then evaporated in vacuo. The oil residue was added into 60 ml 20% aq. HCl and refluxed for another 3 hours. After cooled to room temperature, the precipitate was filtered off. The filtrate was concentrated to about 15 ml in vacuo, then basified to pH 13 to 14 with solid NaOH and extracted with CH2Cl2. The organic layer separated was dried over anhydrous Na2SO4 and concentrated in vacuo to give 1.75 g (31%) 1-amino-3-(cyclohexyl(methyl)amino)propan-2-ol as a colorless liquid.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customevaporated in vacuo
  3. additionThe oil residue was added into 60 ml 20% aq. HCl
  4. temperaturerefluxed for another 3 hours
  5. filtrationthe precipitate was filtered off
  6. concentrationThe filtrate was concentrated to about 15 ml in vacuo
  7. extractionextracted with CH2Cl2
  8. customThe organic layer separated
  9. dry with materialwas dried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-761c9c6bcac44fceb8e533c015dc0043
Source dataset
uspto-grants-2011_12
Patent number
US08084621B2

Reaction notes

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