Hydrochloric Acid → HCID 67422995, compound

HRID 1987331Notes

Reaction equation

HRID 1987331 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:14][CH:13]=[CH:12][CH2:11][CH:10]([C:15]3[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=3)[N:9]2C(=O)C(F)(F)F)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl>CO>[CH3:1][C:2]1[C:3]([CH:8]2[CH2:14][CH:13]=[CH:12][CH2:11][CH:10]([C:15]3[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=3)[NH:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86597123HCID 86597123, compound

Product 1

HCID 67422995HCID 67422995, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[2,7-bis-(3-methyl-pyridin-2-yl)-2,3,6,7-tetrahydro-azepin-1-yl]-2,2,2-trifluoroethanone (73 mg, 0.194 mmol) was dissolved in MeOH (8 mL) and 6N HCl (2 mL) and was heated to 65° C. for 5 hours. The mixture turned black in color. The solvent was removed in vacuo and the residue was basified with 10 N NaOH solution. The mixture was extracted with CH2Cl2 (3×50 mL). The organic extracts were dried (MgSO4), filtered and concentrated. The residue was purified by radial chromatography (1 mm plate, 1:5 EtOAc:hexanes then EtOAc then 10:1 EtOAc/MeOH) to provide 30.2 mg of 2,7-bis-(3-methyl-pyridin-2-yl)-2,3,6,7-tetrahydro-1H-azepine. 1H NMR(CDCl3) δ 2.29-2.36 (m 3H), 2.41 (6H, s), 3.04 (dd, 2H, J=16.2, 10.2 Hz), 5.15 (d, 2H, J=15.6 Hz), 5.81-5.90 (m, 2H), 7.04 (dd, 2H, J=7.5, 4.2 Hz), 7.43 (d, 2H, J=7.5 Hz), 8.35 (d, 2H, J=4.2 Hz).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionThe mixture was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by radial chromatography (1 mm plate, 1:5 EtOAc

Sources & evidence

ORD record
ord-5c0caff2d1c14920bccf553fb0d4f84c
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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