Methylamine → HCID 21031098, compound

HRID 2218047Notes

Reaction equation

HRID 2218047 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 46%

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-fe3354ad7a084436a417a361d1d99906
Source dataset
uspto-grants-2008_08
Patent number
US07410968B2

Reaction notes

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