Trifluoroacetic acid → HCID 89726123, compound

HRID 926386Notes

Reaction equation

HRID 926386 reaction equation
C(OC(N1CCNC[C@@H]1C)=O)(C)(C)C.FC(F)(F)CCI.C(N(CC)CC)C.C(=O)([O-])O.[Na+].C(OC([N:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][C:49]([F:52])([F:51])[F:50])[CH2:43][C@@H:42]1[CH3:53])=O)(C)(C)C.[F:54][C:55]([F:60])([F:59])[C:56]([OH:58])=[O:57]>C(#N)C.ClCCl>[F:54][C:55]([F:60])([F:59])[C:56]([OH:58])=[O:57].[CH3:53][C@@H:42]1[NH:41][CH2:46][CH2:45][N:44]([CH2:47][CH2:48][C:49]([F:52])([F:50])[F:51])[CH2:43]1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 1561651,1,1-Trifluoro-3-iodopropaneHCID 516892Sodium BicarbonateHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylateHCID 118931423HCID 118931423, compound

Product 1

HCID 89726123HCID 89726123, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 1 mmol), 1,1,1-trifluoro-3-iodo-propane (268 mg, 1.2 mmol) and triethylamine (200 mg, 2 mmol) in acetonitrile (10 ml) was stirred at 80° C. for 3 days. After standard work-up (aqueous sodium hydrogencarbonate, dichloromethane), (S)-2-methyl-4-(3,3,3-trifluoro-propyl)piperazine-1-carboxylic acid tert-butyl ester was deprotected under standard conditions with trifluoroacetic acid (1 h) to give (S)-3-methyl-1-(3,3,3-trifluoro-propyl)-piperazine trifluoroacetic acid salt which was used without purification in the next step. LC/MS (method 7): Rt=0.07 min; m/z=197.2 (M+H+).

Sources & evidence

ORD record
ord-3d5ef4dd5b3a408abacc7d4d8395fcc6
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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