Potassium Carbonate → {3-[7-(4-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-propyl}-carbamic acid tert-butyl ester

HRID 2078440Notes

Reaction equation

HRID 2078440 reaction equation
Cl.[CH:2]12[O:10][CH:6]([CH2:7][NH:8][CH2:9]1)[CH2:5][N:4]([CH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH2:3]2.Br[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:27]([O:26][C:25](=[O:31])[NH:24][CH2:23][CH2:22][CH2:21][N:8]1[CH2:9][CH:2]2[O:10][CH:6]([CH2:5][N:4]([CH2:11][C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[CH2:3]2)[CH2:7]1)([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 670966964-(9-Oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl-methyl)-benzonitrile hydrochloride

Product 1

HCID 15980222{3-[7-(4-Cyano-benzyl)-9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl]-propyl}-carbamic acid tert-butyl esterYield 110.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 4-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl-methyl)benzonitrile hydrochloride (6.8 g, 0.021 mol; see Preparation J above), tert-butyl (3-bromopropyl)carbamate (3.93 g, 0.017 mol; see Preparation I above) and dry K2CO3 (8.24 g, 0.059 mol) in 27 mL of dry acetonitrile was stirred at 60° C. overnight under a N2 atmosphere. The reaction mixture was filtered through Celite® and the filtrate was concentrated under reduced pressure to give 7.5 g of the sub-title compound as pale a liquid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cf200db1d7054c2188258b1c612fe30f
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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