Hydrochloric Acid → tert-Butyl 4-cyclopropylpiperazine-1-carboxylate

HRID 1389990Notes

Reaction equation

HRID 1389990 reaction equation
[C:1]([O:5][C:6]([O:8]N=C(C1C=CC=CC=1)C#N)=O)([CH3:4])([CH3:3])[CH3:2].[CH:19]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21][CH2:20]1.Cl>C(OCC)(=O)C>[CH:19]1([N:22]2[CH2:27][CH2:26][N:25]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:8])[CH2:24][CH2:23]2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 47420041-Cyclopropylpiperazine

Product 1

HCID 20294524tert-Butyl 4-cyclopropylpiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Solid 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile (3.2 g, 0.013 mole) was added in one portion to a solution of 1.5 g (0.012 mole) 1-cyclopropylpiperazine in 30 ml ethyl acetate. The solution was stirred at room temperature for 3 hours and then treated with 100 ml dilute aqueous HCl. The aqueous phase was separated, extracted with additional ethyl acetate (discarded), treated with excess 10% NaOH, and extracted with ether. The ether extracts were dried (MgSO4), filtered, and evaporated in vacuo to yield a semi-solid residue. Recrystallization from hexane at -70° C. gave 1.9 g white, crystalline solid, m.p. 65°-67° C. Calculated for C12H22N2O2 (226.32): C, 63.98; H, 9.80; N, 12.38; O, 14.14. Found: C, 63.82; H, 9.82; N, 12.60; O, 13.90.

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with additional ethyl acetate (discarded)
  3. additiontreated with excess 10% NaOH
  4. extractionextracted with ether
  5. dry with materialThe ether extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto yield a semi-solid residue
  9. customRecrystallization from hexane at -70° C.
  10. customgave 1.9 g white

Sources & evidence

ORD record
ord-82afb58bf6d64234a4dd4f1e71c48165
Source dataset
uspto-grants-1981_01
Patent number
US04247549

Reaction notes

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