Methylamine → HCID 21031098, compound

HRID 1829679Notes

Reaction equation

HRID 1829679 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 0-{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-c2d510d6624a41b899dbaa6680018610
Source dataset
uspto-grants-2006_06
Patent number
US07064129B2

Reaction notes

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