Methylamine → HCID 21031098, compound

HRID 2220898Notes

Reaction equation

HRID 2220898 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[S:27])[N:24]([CH3:26])[CH3:25])=[CH:18][CH:17]=1.CN>>[NH2:3][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23](=[S:27])[N:24]([CH3:25])[CH3:26])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 58912942HCID 58912942, compound

Product 1

HCID 21031098HCID 21031098, compoundYield 58.4%

Procedure

A mixture of dimethylthiocarbamic acid O-{4-[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-butyl]phenyl}ester 9 (0.30 g, 0.80 mmol) and methylamine (2M in methanol, 10 mL, 20 mmol) was stirred at room temperature overnight. Solvent was removed by rotary evaporation and the residue was purified by flash silica gel column chromatography (Biotage) eluting with chloroform/methanol/concentrated ammonium hydroxide (10:1:0.1, v/v) to give dimethylthiocarbamic acid O-[4-(4-aminobutyl)phenyl]ester (10) as a clear colorless oil (118 mg, 46% yield). 1H NMR (300 MHz, CD3OD) δ 1.70 (m, 4H), 2.70 (m, 4H), 3.34 (s, 3H), 3.46 (s, 3H), 6.96 (d, 2H), 7.20 (d, 2H). m/z (ESI): 253 [C13H20N2OS+H]+.

Workup

  1. customSolvent was removed by rotary evaporation
  2. customthe residue was purified by flash silica gel column chromatography (Biotage)
  3. washeluting with chloroform/methanol/concentrated ammonium hydroxide (10:1:0.1

Sources & evidence

ORD record
ord-6d6e530e3e4b4e279bd3f3bd0de178ae
Source dataset
uspto-grants-2008_05
Patent number
US07368447B2

Reaction notes

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