Methanol → Methyl 12-aminododecanoate--hydrogen chloride (1/1)

HRID 72097

Reaction equation

HRID 72097 reaction equation
O=S(Cl)[Cl:3].[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[CH3:20]O>>[ClH:3].[CH3:20][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH2:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 6966112-Aminododecanoic Acid

Product 1

HCID 19372000Methyl 12-aminododecanoate--hydrogen chloride (1/1)Yield 60%

Procedure

MeOH (40 ml) was cooled to 0-5° C., and SOCl2 (4 ml) was added drop wise with stirring during 30 minutes. 12-Aminododecanoic acid (3 g, 13.9 mmol) was added and the resulting suspension was stirred at 0-5° C. while the ice in cooling bath melted and allowed to warm to room temperature during 16 hours. The mixture was filtered and the solid was dried by suction to afford 2.23 g (60%) of 12-aminododecanoic acid methyl ester hydrochloride. From the mother liquor a further batch of 0.92 g (25%) was isolated.

Workup

  1. temperaturein cooling bath
  2. filtrationThe mixture was filtered
  3. customthe solid was dried by suction

Sources & evidence

ORD record
ord-e32181550fca4c63a91217fa119ba77b
Source dataset
uspto-grants-2014_09
Patent number
US08828923B2

Linked notes

Loading…