Hydrochloric Acid → 4-[3-(3,7-Diazabicyclo[3.3.1]non-3-yl)-2-hydroxypropoxy]benzonitrile

HRID 1596433Notes

Reaction equation

HRID 1596433 reaction equation
Cl.[C:2]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH:10]([OH:28])[CH2:11][N:12]2[CH2:19][CH:18]3[CH2:20][CH:14]([CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17]3)[CH2:13]2)=[CH:6][CH:5]=1)#[N:3]>CCOC(C)=O>[CH:14]12[CH2:20][CH:18]([CH2:17][NH:16][CH2:15]1)[CH2:19][N:12]([CH2:11][CH:10]([OH:28])[CH2:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:30][CH:29]=1)[CH2:13]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53796099HCID 53796099, compound

Product 1

HCID 217019464-[3-(3,7-Diazabicyclo[3.3.1]non-3-yl)-2-hydroxypropoxy]benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

HCl-saturated EtOAc (600 mL) was added to a solution of tert-butyl 7-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (62 g; see Example 2 below) in EtOAc (600 mL) and the mixture was stirred at rt. for 4 h. The solvent was removed under reduced pressure, the residue was dissolved in MeCN (1.3 L) and K2CO3 (100 g) was added. The suspension was stirred for 12 h and filtered. Concentration of the filtrate gave the title compound in a 90% yield.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in MeCN (1.3 L)
  3. additionK2CO3 (100 g) was added
  4. stirringThe suspension was stirred for 12 h
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5c92d3e1de204a6e9ae1a14d8cc0f618
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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