Acetyl chloride → 1-Acetylamino-3-adamantanol

HRID 1937256

Reaction equation

HRID 1937256 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][C:15]([OH:23])([CH2:16]3)[CH2:14]1)[CH2:20]2>C1COCC1.CN(C=O)C>[C:1]([NH:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][C:15]([OH:23])([CH2:16]3)[CH2:14]1)[CH2:20]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 6586453-Amino-1-adamantanol2×

Product 1

HCID 28427921-Acetylamino-3-adamantanolYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

In an atmosphere of nitrogen, 11 mmole of acetyl chloride and 12 mmole of triethylamine were dissolved in 2 mL of THF. To the resultant mixture, 10 mmole of a solution of 1-amino-3-adamantanol in DMF (10 mL) was added dropwise over 30 minutes at 40° C. The mixture was stirred for another 3 hours at 40° C. As a result, the conversion of 1-amino-3-adamantanol was 99%, and 1-acetylamino-3-adamantanol (yield 95%) was formed.

Sources & evidence

ORD record
ord-9fe3d2d1de57459dbb32fb35bbc49da9
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Linked notes

Loading…