Hydrochloric Acid → 1-(1-(4-Oxocyclohexyl)propyl)urea

HRID 2175608Notes

Reaction equation

HRID 2175608 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([CH:11]([NH:14][C:15]([NH2:17])=[O:16])[CH2:12][CH3:13])[CH2:7][CH2:6]2)[O:4]CC1.Cl>CC#N>[O:4]=[C:5]1[CH2:6][CH2:7][CH:8]([CH:11]([NH:14][C:15]([NH2:17])=[O:16])[CH2:12][CH3:13])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68003780HCID 68003780, compound

Product 1

HCID 680035921-(1-(4-Oxocyclohexyl)propyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (1-1,4-dioxaspiro[4.5]decan-8-ylpropyl)urea (as prepared in the previous step, 89 mg, 0.37 mmol, 1.00 equiv) in CH3CN (2 mL) and HCl (2M, 2 mL) was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was diluted with 20 mL of aq. sodium bicarbonate (1M). The resulting solution was extracted with 2×20 ml, of dichloromethane. The organic layers were combined, dried and concentrated under vacuum to give the title compound as a yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additionThe residue was diluted with 20 mL of aq. sodium bicarbonate (1M)
  3. extractionThe resulting solution was extracted with 2×20 ml, of dichloromethane
  4. customdried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6f40b78c973243879f3571e24aec6dbc
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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