Hexachloroethane → HCID 86686951, compound

HRID 2282362Notes

Reaction equation

HRID 2282362 reaction equation
ClC(Cl)(Cl)C(Cl)(Cl)Cl.[F:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][NH:17][C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=O)=[N:14][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C1COCC1>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[N:17][N:16]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86686950Piperidine-1-carboxylic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Product 1

HCID 86686951HCID 86686951, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hexachloroethane (826 mg, 3.92 mmol) was added portionwise to a solution of Intermediate 3a (466 mg, 1.95 mmol), triphenylphosphine (1.03 g, 3.92 mmol) and triethylamine (1.1 mL, 7.83 mmol) in dry THF (30 mL) at RT, and the mixture stirred for 2 h. The resulting precipitate was filtered off and the filtrate evaporated. The residue was purified by SCX-2, eluting with MeOH followed by 2M NH3 in MeOH, to give the title compound as pale orange coloured gum (206 mg, 48%). LCMS (Method 1): Rt 2.44 min, m/z 221 [MH+].

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customthe filtrate evaporated
  3. customThe residue was purified by SCX-2
  4. washeluting with MeOH

Sources & evidence

ORD record
ord-a192c04974c34e8faf4026e821ff4db5
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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