Chloroacetonitrile → HCID 86052733, compound

HRID 600467Notes

Reaction equation

HRID 600467 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[C:7]1[CH2:12][CH2:11][N:10]([C:13](OC(C)(C)C)=O)[CH2:9][CH2:8]1.O1CCOCC1.[CH2:32]([N:34](CC)CC)C.ClCC#N>Cl.C1COCC1>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[C:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:32]#[N:34])[CH2:11][CH2:12]1

Participants

7

Reactant 4

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 59729293HCID 59729293, compound

Product 1

HCID 86052733HCID 86052733, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-((1,3,4-oxadiazol-2-yl)(phenyl)methylene)piperidine-1-carboxylate (100 mg, 0.29 mmol) was diluted with 4 M HCl in 1,4-dioxane (1.2 mL, 4.8 mmol) and stirred 1 h. The reaction was concentrated and the residue diluted with THF (1.5 mL), triethylamine (0.5 mL, 3.8 mmol) and chloroacetonitrile (0.25 mL, 3.9 mmol). The reaction was stirred 3 d, concentrated, diluted with MeOH, filtered and purified by preparative HPLC to yield 45 (43 mg, 0.15 mmol, 53%) as a white solid. 1H NMR: (500 MHz, CDCl3) δ 8.27 (s, 1H), 7.41-7.31 (m, 3H), 7.20-7.16 (m, 2H), 3.55 (s, 2H), 3.02 (t, J=5.8 Hz, 2H), 2.75 (t, J=5.8 Hz, 2H), 2.61 (t, J=5.8 Hz, 2H), 2.39 (t, J=5.8 Hz, 2H); LC/MS: (ES+) m/z (M+H)=281; HPLC Rt=0.97 min., column G, conditions B.

Workup

  1. concentrationThe reaction was concentrated
  2. stirringThe reaction was stirred 3 d
  3. concentrationconcentrated
  4. additiondiluted with MeOH
  5. filtrationfiltered
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-50bc13356c4d4d34a104e2ae8713766e
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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