Hydrochloric Acid → 799559-60-7

HRID 734324Notes

Reaction equation

HRID 734324 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C1C=CC2N(O)N=NC=2C=1.[CH3:28][C@@H:29]1[CH2:34][NH:33][CH2:32][C@H:31]([CH3:35])[NH:30]1.[ClH:36]>CN(C=O)C.C(Cl)Cl.C(OCC)C.C(Cl)CCl>[ClH:36].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([C:15]([N:33]3[CH2:32][C@H:31]([CH3:35])[NH:30][C@H:29]([CH3:28])[CH2:34]3)=[O:17])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1)#[N:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 193914381-(4-Cyanophenyl)piperidine-4-carboxylic acid

Product 1

HCID 68816962799559-60-7

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-(4-Cyanophenyl)-piperidine4-carboxylic acid (D3)(6.92 g), HOBT (1.77 g), TEA (4.7 ml) and (2R,6S)-2,6-dimethylpiperazine (3.0 g) were stirred in DMF (25 ml) and then EDC (3.7 g) was added and the reaction stirred at rt overnight. The solvent was evaporated and the residue redissolved in DCM (100 ml) and washed with saturated sodium hydrogen carbonate (2×80 ml), brine (75 ml) and the organic layer dried (MgSO4) and evaporated. The crude product was then purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM]. Fractions containing the required product were evaporated to give the free base compound which was dissolved in DCM (10 ml) and treated with 1N HCl in diethyl ether to give the title compound (D13) as a white precipitate which was filtered off (1.80 g). MS electrospray (+ve) 327 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in DCM (100 ml)
  3. washwashed with saturated sodium hydrogen carbonate (2×80 ml), brine (75 ml)
  4. dry with materialthe organic layer dried (MgSO4)
  5. customevaporated
  6. customThe crude product was then purified by column chromatography [silica gel, step gradient 0-10% MeOH (containing 10% 0.880 ammonia solution) in DCM]
  7. additionFractions containing the required product
  8. customwere evaporated
  9. customto give the free base compound which

Sources & evidence

ORD record
ord-e34432d33ef342b486c6861bac1b80d8
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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