Trifluoroacetic acid → HCID 18328972, compound

HRID 1249812Notes

Reaction equation

HRID 1249812 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]23[CH2:27][CH:22]4[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]4)[CH2:19]2)[CH2:25]3)[C:13](=[O:28])[CH2:12]1)=O)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[C:18]12([CH2:17][N:14]3[CH2:15][CH2:16][NH:11][CH2:12][C:13]3=[O:28])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18328966HCID 18328966, compound

Product 1

HCID 18328972HCID 18328972, compound

Procedure

4-Benzyloxycarbonyl-[1-((adamant-1-yl)methyl)]-piperazin-2-one (300.0 mg, 0.9 mmol), prepared as described in Step 3, was dissolved into neat trifluoroacetic acid(5.0 ml) and the reaction allowed to stir for 30 minutes. Excess trifluoroacetic acid was removed under high vacuum and the resulting gum treated with 4.0N HCl in dioxane and after 10 minutes excess solvents were removed under high vacuum to give 1-((adamant-1-yl)methyl)piperazin-2-one as the hydrochloride salt. 400 Mhz H1 NMR (CD3OD): 1.62(s, 6H),1.68-1.77 (m,6H), 1.97(br s,3H), 3.16(s, 2H), 3.52(t, 2H), 3.72(t,2H), 3.86(s, 2H). High res. FAB MS: Theoretical Mass 249.1961, Measured Mass 249.1952(C15H24N2O+H+).

Workup

  1. customExcess trifluoroacetic acid was removed under high vacuum
  2. additionthe resulting gum treated with 4.0N HCl in dioxane and after 10 minutes excess solvents
  3. customwere removed under high vacuum

Sources & evidence

ORD record
ord-c2441eedde4745609b7cf7f88bdeddc8
Source dataset
uspto-grants-2002_01
Patent number
US06335343B1

Reaction notes

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