Nitrogen → Ammonium Hydroxide

HRID 1743712Notes

Reaction equation

HRID 1743712 reaction equation
C([N:8]1[CH2:14][CH:13]2[N:15]([CH2:16][CH2:17][CH2:18][CH:19]([C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=3)[O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)C1C=CC=CC=1.N#N.C(Cl)Cl.C(Cl)(Cl)Cl.CO.CC(O)=O>CO.[Pd].CC(O)=O>[NH4+:8].[OH-:20].[CH:10]12[N:15]([CH2:16][CH2:17][CH2:18][CH:19]([C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=3)[O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=3)[CH:13]([CH2:12][CH2:11]1)[CH2:14][NH:8][CH2:9]2

Participants

9

Reactant 4

HCID 947NitrogenHCID 6344DichloromethaneHCID 21866353chloroform methanol HOAcHCID 22235385HCID 22235385, compound

Product 2

HCID 14923Ammonium HydroxideHCID 22235578HCID 22235578, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

To a solution of 4-[4-(3-benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-1-(3,4-dimethoxyphenoxy)butyl]benzonitrile (9.2 g, 15.7 mmol; from step (d) above) in MeOH (1000 mL) was added 10% Pd/C (2.8 g) under a blanket of N2. The resulting solution was purged with H2 then stirred under a H2 atmosphere for 2 h. The solution was filtered through Celite® and the filtrate concentrated in vacuo to give a crushable foam. Flash chromatography on silica gel eluting first with CH2Cl2:MeOH:concentrated NH4OH (188:10:2 to 177:20:3 gradient) then a second flash chromatography with CHCl3:MeOH:AcOH (90:10:1 to 85:10:5 to 50:45:5 gradient) gave the AcOH salt of the title compound. The AcOH salt was neutralized with aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to afford 3.2 g (48%) of the title compound.

Workup

  1. customThe resulting solution was purged with H2
  2. filtrationThe solution was filtered through Celite®
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a crushable foam

Sources & evidence

ORD record
ord-1a529062bfae4cdaa13e756261452cb6
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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