Hydrochloric Acid → HCID 68965351, compound

HRID 2378938Notes

Reaction equation

HRID 2378938 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1.[ClH:24]>O>[ClH:24].[NH:11]1[CH2:10][CH2:9][CH:8]([N:7]2[CH:3]=[CH:4][NH:5][C:6]2=[O:21])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59006379HCID 59006379, compound

Product 1

HCID 68965351HCID 68965351, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl 4-(3-(2,2-dimethoxyethyl)ureido)piperidine-1-carboxylate (1.62 g, 4.89 mmol) was suspended in water (15 ml). Concentrated hydrochloric acid (15 ml, 183 mmol) was added to the mixture. Reaction was held at room temperature for 20 minutes. Mixture was concentrated by roto-vap. Residue was treated with ethanol and the mixture was then concentrated by roto-vap. Residue was treated with ethyl acetate and then concentrated to dryness. Resulting yellow oil was triturated in 80% acetone-diethyl ether. After 10 minutes a consistent solid was formed. Solids were filtered off and washed with acetone. Solids were dried in vacuo. Title compound was obtained as off-white solid in 99% yield. MS (M+H)+=168.1.

Workup

  1. customReaction
  2. concentrationMixture was concentrated by roto-vap
  3. additionResidue was treated with ethanol
  4. concentrationthe mixture was then concentrated by roto-vap
  5. additionResidue was treated with ethyl acetate
  6. concentrationconcentrated to dryness
  7. customResulting yellow oil
  8. customwas triturated in 80% acetone-diethyl ether
  9. customAfter 10 minutes a consistent solid was formed
  10. filtrationSolids were filtered off
  11. washwashed with acetone
  12. customSolids were dried in vacuo

Sources & evidence

ORD record
ord-babe313c37ac4a42afe98212c42e954b
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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