Dimethylamine → HCID 21031127, compound

HRID 2218059Notes

Reaction equation

HRID 2218059 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:9][CH:8]=1)C.[CH3:29][NH:30][CH3:31]>>[CH2:21]([O:20][C:18](=[O:19])[NH:17][CH2:16][CH2:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4](=[O:3])[N:30]([CH3:31])[CH3:29])=[CH:8][CH:9]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 21031128[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester

Product 1

HCID 21031127HCID 21031127, compoundYield 52%

Conditions

Temperature
55 °C

Procedure

A mixture of [4-(4-benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester 23 (0.50 g, 1.3 mmol) and dimethylamine (2.0 M in THF, 10 mL, 20 mmol) in a sealed tube was heated at 55° C. for 48 h. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/CH2Cl2, 1:4, 1:3, v/v) to provide [4-(4-dimethylcarbamoylmethoxyphenyl)butyl]carbamic acid benzyl ester 28 (0.26 g, 52% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 2.55 (m, 4H), 2.55 (m, 2H), 2.90 (s, 3H), 3.05 (s, 3H), 3.20 (m, 2H), 4.65 (s, 2H), 5.08 (s, 2H), 6.80 (d, 2H), 7.05 (d, 2H), 7.35 (m, 5H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/CH2Cl2, 1:4, 1:3

Sources & evidence

ORD record
ord-a4c022fe6e2b4167a88bc0cec0782066
Source dataset
uspto-grants-2008_08
Patent number
US07410968B2

Reaction notes

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