Trifluoroacetic acid → {2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amine

HRID 553482Notes

Reaction equation

HRID 553482 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][O:30][CH3:31])=[CH:25][CH:24]=3)=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:31][O:30][CH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[C:17]([N:14]3[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][NH:7][CH3:6])[CH2:16][CH2:15]3)=[N:18][CH:19]=[CH:20][N:21]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67366660{2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-carbamic acid tert-butyl ester

Product 1

HCID 67367004{2-[3'-(4-Methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve {2-[3′-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-carbamic acid tert-butyl ester (1.01 g, 2.3 mmol, 1 eq.) in dichloromethane (20 mL). Add trifluoroacetic acid (10.5 g, 7.1 mL, 92 mmol, 40 eq.). Stir at room temperature for 1.5 hr. Partition the reaction mixture between aqueous 5N NaOH (pH aqueous layer=14) and dichlormethane. Separate the layers. Extract the aqueous layer with dichloromethane (2×50 mL). Combine the organic layers, dry over anhydrous Na2SO4, filter and concentrate to afford the title preparation (0.76 g, 97% yield). MS (loop): m/z=342.3 [M+H].

Workup

  1. customPartition the reaction mixture between aqueous 5N NaOH (pH aqueous layer=14) and dichlormethane
  2. customSeparate the layers
  3. extractionExtract the aqueous layer with dichloromethane (2×50 mL)
  4. dry with materialCombine the organic layers, dry over anhydrous Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto afford the title
  8. custompreparation (0.76 g, 97% yield)

Sources & evidence

ORD record
ord-2b7580d59a4d41b287196fa5a1c7f94c
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

Loading…