Ammonia → HCID 178480306, compound

HRID 2371156Notes

Reaction equation

HRID 2371156 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH3:25])[CH2:20]3)[CH2:14][CH2:13]2)=S)[CH:5]=[CH:6][C:7]=1[Cl:8].CO.[NH3:28]>C1COCC1.ClCCl.[O-]S(C(F)(F)F)(=O)=O.[Ag+]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH3:25])[CH2:20]3)[CH2:14][CH2:13]2)=[NH:28])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 57656911N-(3,4-Dichlorophenyl)-4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carbothioamide

Product 1

HCID 178480306HCID 178480306, compound

Reagents, catalysts & solvents 3

HCID 76223Silver(I) trifluoromethanesulfonateCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

N-(3,4-Dichlorophenyl)-4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carbothioamide (0.53 g) was dissolved in a mixture of saturated ammonia in THF (1 ml) and dichloromethane (20 ml). The reaction mixture was cooled to −30° C. under an atmosphere of argon then silver triflate (0.34 g) was added. The reaction mixture was allowed to warm to room temperature then methanol (4 ml) was added. The soluble material was separated the concentrated in vacuo. The crude product was subjected to reverse phase HPLC using a gradient of 95% water/acetonitrile/0.1% TFA through to 50% water/acetonitrile/0.1% TFA. The combined product fractions were concentrated in vacuo then separated between dichloromethane (50 ml) and saturated sodium bicarbonate solution (100 ml). The dichloromethane layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo to give the title compound (209.1 mg).

Workup

  1. temperatureto warm to room temperature
  2. customThe soluble material was separated the
  3. concentrationconcentrated in vacuo
  4. concentrationThe combined product fractions were concentrated in vacuo
  5. customthen separated between dichloromethane (50 ml) and saturated sodium bicarbonate solution (100 ml)
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e54547a2309444adaf3e9b4b4f993456
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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