4-Methylmorpholine → HCID 89677103, compound

HRID 2278167Notes

Reaction equation

HRID 2278167 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[CH3:29])[N:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[C:4]([CH3:30])[CH:3]=1.CN1CCOCC1.[Si](I)(C)(C)C>C(Cl)Cl>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:30])[N:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[C:23]([CH3:29])[CH:24]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 85247Trimethylsilyl iodideHCID 89676816HCID 89676816, compound

Product 1

HCID 89677103HCID 89677103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with tert-butyl 4-(bis(4-chloro-2-methylphenyl)methyl)piperazine-1-carboxylate (184 mg, 409 mmol), CH2Cl2 (5 mL), and NMM (90 μL, 0.819 mmol). Cooled to 0° C. and added TMSI (70 μL, 0.491 mmol) dropwise. After 15 min at 4° C. the reaction was quenched with sat Na2CO3 and extracted with CH2Cl2 (3×). The organics were dried (Na2SO4), filtered, and concentrated. The residue was chromatographed on a silica gel column (100% CH2Cl2 to 6% 2M NH3 in MeOH) and 1-(bis(4-chloro-2-methylphenyl)methyl)piperazine (143 mg, 70%). 1H NMR 400 MHz (CDCl3) δ 7.47 (dd, J=8.4, 1.1 Hz, 2H), 7.16-7.11 (m, 1H), 7.11-7.06 (m, 2H), 4.64 (s, 1H), 2.88-2.80 (m, 4H), 2.44-2.33 (m, 5H), 2.28 (s, 7H). LCMS (ESI, m/z): 349 [M+H]+.

Workup

  1. customAfter 15 min at 4° C. the reaction was quenched with sat Na2CO3
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a silica gel column (100% CH2Cl2 to 6% 2M NH3 in MeOH) and 1-(bis(4-chloro-2-methylphenyl)methyl)piperazine (143 mg, 70%)

Sources & evidence

ORD record
ord-70a4adfc721842ed9d8282f490500a28
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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