Dichloromethane → N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide

HRID 603210Notes

Reaction equation

HRID 603210 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][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].FC(F)(F)C(O)=O.ClCCl.C([O-])(O)=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57656932tert-Butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidine-1-carboxylate

Product 1

HCID 57656731N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamideYield 67.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

tert-Butyl (3S)-3-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]piperidine-1-carboxylate (1 g), trifluoroacetic acid (10 ml) and dichloromethane (20 ml) were stirred at room temperature for one hour. The solvent was removed in vacuo to yield a dark brown oil. Water (20 ml) was added to this giving a milky solution and this was then basified to ˜pH 6 by addition of solid NaHCO3. This left a milky solution which was diluted with water (˜50 ml) before extracting with ethyl acetate (3×75 ml). The combined organics were washed with brine (˜100 ml) and separated then dried (MgSO4) before removing solvent in vacuo to yield the title compound (531 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield a dark brown oil
  3. waitThis left a milky solution which
  4. extractionbefore extracting with ethyl acetate (3×75 ml)
  5. washThe combined organics were washed with brine (˜100 ml)
  6. customseparated
  7. dry with materialthen dried (MgSO4)
  8. custombefore removing solvent in vacuo

Sources & evidence

ORD record
ord-bf5b91f7c585406bbb30a1f4c465dce2
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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