Methylamine → HCID 21031098, compound

HRID 132551Notes

Reaction equation

HRID 132551 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 chloroformr/methanol/concentrated ammonium hydroxide (10:1:0.1, v/v) to give dimethylthiocarbamic acid 0-[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 chloroformr/methanol/concentrated ammonium hydroxide (10:1:0.1

Sources & evidence

ORD record
ord-3ed5da95d79b47cb92d340227037a4c7
Source dataset
uspto-grants-2008_06
Patent number
US07388013B2

Reaction notes

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