Triethylamine → HCID 22498786, compound

HRID 1814741Notes

Reaction equation

HRID 1814741 reaction equation
Cl.[NH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].C(N(CC)CC)C.[CH3:19][C:20]([CH3:24])([CH3:23])[CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 122918142-Amino-1-(morpholin-4-yl)ethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 22498786HCID 22498786, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the above 2-amino-1-morpholin-4-yl-ethanone hydrochloride (0.23 g, 1.3 mmol) in methylene chloride (4.0 mL) and triethylamine (0.19 mL, 1.4 mmol), 4 angstrom sieves (10 beads, pulverized to a powder) were added, followed by trimethylacetaldehyde (0.35 mL, 3.3 mmol) at room temperature, under argon. The resulting mixture was stirred at room temperature overnight after which time sodium triacetoxyborohydride (0.54 g, 2.6 mmol) was added. After 6 h, the solids were removed via filtration and washed with methylene chloride. The combined filtrates were concentrated and the remaining residue was diluted with EtOAc and water. The aqueous phase was lyophilized to give a white solid that was diluted with EtOAc. The solids were removed via filtration and washed with EtOAc. The combined organics were concentrated to give the crude product which was purified via silica gel flash chromatography eluting with 100% EtOAc, then 0.5% NH4OH/10% MeOH/EtOAc, flow rate 30 mL/min. The product-containing fractions were concentrated to give 0.18 g (67%) of 2-(2,2-dimethyl-propylamino)-1-morpholin-4yl-ethanone.

Workup

  1. additionwere added
  2. additionwas added
  3. customthe solids were removed via filtration
  4. washwashed with methylene chloride
  5. concentrationThe combined filtrates were concentrated
  6. additionthe remaining residue was diluted with EtOAc and water
  7. customto give a white solid
  8. customThe solids were removed via filtration
  9. washwashed with EtOAc
  10. concentrationThe combined organics were concentrated
  11. customto give the crude product which
  12. customwas purified via silica gel flash chromatography
  13. washeluting with 100% EtOAc
  14. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-c377b1dd923a445a9ba22b41747fc979
Source dataset
uspto-grants-2005_04
Patent number
US06878706B1

Reaction notes

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