Potassium Carbonate → HCID 89676816, compound

HRID 2278166Notes

Reaction equation

HRID 2278166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[CH3:17])O)=[C:4]([CH3:18])[CH:3]=1.S(Cl)(Cl)=O.[N:23]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+]>[Cl-].[Na+].O.C(#N)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[CH3:17])[N:26]2[CH2:25][CH2:24][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27]2)=[C:4]([CH3:18])[CH:3]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10062236HCID 10062236, compound

Product 1

HCID 89676816HCID 89676816, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A round bottom flask was charged with bis(4-chloro-2-methylphenyl)methanol (200 mg, 0.711 mmol) and CH2Cl2 (7 mL). Thionyl chloride (100 μL, 1.37 mmol) was added and the reaction was stirred at room temperature for 24 h. The reaction was concentrated. Acetonitrile was added and the reaction was concentrated two times. Acetonitrile (6 mL), tert-butyl piperazine-1-carboxylate (200 mg, 1.07 mmol) and K2CO3 (200 mg, 1.42 mmol) were added and the reaction was heated to 80° C. for 4 h and 120° C. for 18 h. The reaction was poured into brine and extracted with EtOAc (2×). The residue was chromatographed on a silica gel column (100% hexanes to 20% EtOAc) and yielded the title (184 mg, 57%) as a clear oil. 1H NMR 400 MHz (CDCl3) δ 7.49 (d, J=8.4 Hz, 2H), 7.16 (d, J=8.4 Hz, 2H), 7.11 (s, 2H), 4.65 (s, 1H), 3.44-3.37 (m, 4H), 2.38 (s, 4H), 2.29 (s, 6H), 1.46 (s, 9H). LCMS (ESI, m/z): 471 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additionAcetonitrile was added
  3. concentrationthe reaction was concentrated two times
  4. temperaturethe reaction was heated to 80° C. for 4 h and 120° C. for 18 h
  5. extractionextracted with EtOAc (2×)
  6. customThe residue was chromatographed on a silica gel column (100% hexanes to 20% EtOAc)
  7. customyielded the title (184 mg, 57%) as a clear oil

Sources & evidence

ORD record
ord-4c86c33d0a964d509a870d26f4b7ec4e
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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