Amantadine → HCID 22639319, compound

HRID 2415004Notes

Reaction equation

[NH2:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.[CH2:12]([N:14]([CH2:43][C:44](O)=[O:45])[S:15]([C:18]([F:42])([F:41])[C:19]([F:40])([F:39])[C:20]([F:38])([F:37])[C:21]([F:36])([F:35])[C:22]([F:34])([F:33])[C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])(=[O:17])=[O:16])[CH3:13].ON1C(=O)CCC1=O>O1CCCC1>[C:2]12([NH:1][C:44](=[O:45])[CH2:43][N:14]([CH2:12][CH3:13])[S:15]([C:18]([F:42])([F:41])[C:19]([F:39])([F:40])[C:20]([F:37])([F:38])[C:21]([F:35])([F:36])[C:22]([F:33])([F:34])[C:23]([F:31])([F:32])[C:24]([F:29])([F:30])[C:25]([F:28])([F:27])[F:26])(=[O:17])=[O:16])[CH2:3][CH:4]3[CH2:10][CH:8]([CH2:7][CH:6]([CH2:5]3)[CH2:11]1)[CH2:9]2

Participants

Conditions

Temperature: 0 °C

Procedure

30.95 g (150 mmol) of N,N-dicyclohexylcarbodiimide is added at 0° C. to 15.12 g (100 mmol) of 1-aminoadamantane, 58.52 g (100 mmol) of N-(ethyl)N-(perfluorooctylsulfonyl)-aminoacetic acid and 11.51 g (100 mmol) of N-hydroxysuccinimide, dissolved in 300 ml of tetrahydrofuran. It is stirred for 2 hours at 0° C., then for 6 hours at room temperature. Precipitated urea is filtered out, the filtrate is evaporated to the dry state, and the residue is chromatographed on silica gel (mobile solvent: dichloromethane/acetone=30:1).

Workup

waitfor 6 hours at room temperature
filtrationPrecipitated urea is filtered out
customthe filtrate is evaporated to the dry state
customthe residue is chromatographed on silica gel (mobile solvent: dichloromethane/acetone=30:1)

Sources & evidence

ORD record: ord-527e05b2b6c84f8cbf2b5a7b33a08af7
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818203B2

Reaction notes

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