Acetic Acid → HCID 86700883, compound

HRID 1396015Notes

Reaction equation

HRID 1396015 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][CH2:10][O:11][CH:12]([CH2:22][O:23]CC1C=CC=CC=1)[CH2:13][O:14]CC1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[ClH:42]>CCO.[Pd]>[ClH:42].[NH2:8][CH2:9][CH2:10][O:11][CH:12]([CH2:22][OH:23])[CH2:13][OH:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67976338HCID 67976338, compound

Product 1

HCID 86700883HCID 86700883, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Charged a solution of N,N-dibenzyl-2-(1,3-bis(benzyloxy)propan -2-yloxy)ethanamine (2000 g, 4.0 mol, 1.0 eq) in EtOH (10000 mL, 5.0 v), Pd/C (10%, 400 g, 20% wt,) and acetic acid (970 g, 16.2 mol, 4.0 eq) to a 20 L pressure reactor. The resulting mixture was stirred for 10 hours at 80° C. under hydrogen (20 atm). The reaction progress was monitored with NMR. The reaction mixture was cooled to 20˜30° C. and filtered. HCl (36%, 500 ml, 6.0 mol, 1.5 eq) was added to the filtrate, stirred for 10 minutes and concentrated under vacuum to give 572 g (83.4%) of 2-(2-aminoethoxy)propane-1,3-diol hydrochloride as an oil. H-NMR of 3 (300 MHz, D2O, ppm): 3.79 (2H, q), 3.60 (2H, m), 3.50 (3H, m), 3.15 (2H, q).

Workup

  1. temperatureThe reaction mixture was cooled to 20˜30° C.
  2. filtrationfiltered
  3. stirringstirred for 10 minutes
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-00f1364586c843b0989e852cec6cbbbd
Source dataset
uspto-grants-2014_12
Patent number
US08901101B2

Reaction notes

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