Methylamine → Adamantan-1-yl-methylamino-acetic acid

HRID 133809Notes

Reaction equation

HRID 133809 reaction equation
[C:1]12([CH:11](I)[C:12]([OH:14])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:16][NH2:17]>O1CCCC1>[C:1]12([CH:11]([NH:17][CH3:16])[C:12]([OH:14])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 13022564Adamantan-1-yl-iodo-acetic acid

Product 1

HCID 11229817Adamantan-1-yl-methylamino-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Adamantan-1-yl-iodo-acetic acid (7.86 g, 24.55 mmol, P. A. Krasutskii. et. Al.;J. Org. Chem. USSR (Engl. Trans.); 1985; 1327-1332) is refluxed with 100 mL of 2M methylamine in tetrahydrofuran for 18 hours. The solvent is evaporated in vacuo, and the residue treated with water. The pH is adjusted to 6 and the resulting solid collected and dried to give 2.16 g of the title compound as a white solid. MS: m/z 224.2 (M+1).

Workup

  1. customThe solvent is evaporated in vacuo
  2. additionthe residue treated with water
  3. customthe resulting solid collected
  4. customdried

Sources & evidence

ORD record
ord-6f5707e218a946dbb1954efdfef1308c
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

Loading…