Potassium Carbonate → {4-[4-(2-Dimethylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 1392929Notes

Reaction equation

HRID 1392929 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>>[CH2:1]([O:8][C:9](=[O:22])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:27][CH2:26][N:25]([CH3:29])[CH3:24])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 11637991N-Cbz4-(4-hydroxyphenyl)butylamine

Product 1

HCID 66849448{4-[4-(2-Dimethylaminoethoxy)phenyl]butyl}carbamic acid benzyl esterYield 61%

Conditions

Temperature
80 °C

Procedure

A mixture of [4-(4-hydroxyphenyl)butyl]carbamic acid benzyl ester (1.5 g, 5 mmol), 2-dimethylaminochloroethane hydrochloride (1.4 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol) and 18-crown-6 ether (154 mg, 0.58 mmol) was stirred at 80° C. (oil bath) for 18 h. After this time, the solvent was removed under reduced pressure and the residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 10:1:0.1 chloroform/methanol/concentrated ammonium hydroxide) to provide 62 (1.1 g, 61%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 1.56 (m, 4H), 2.32 (s, 6H), 2.56 (m, 2H), 2.71 (t, 2H), 3.18 (m, 2H), 4.04 (t, 2H), 4.78 (br s, 1H), 5.08 (s, 2H), 6.83 (d, 2H), 7.06 (d, 2H), 7.35 (m, 5H).

Workup

  1. customAfter this time, the solvent was removed under reduced pressure
  2. customthe residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 10:1:0.1 chloroform/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-1f1dc271aabf4059b012c68c8e85c34a
Source dataset
uspto-grants-2008_03
Patent number
US07345044B2

Reaction notes

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