Diisopropylethylamine → (E)-3-(5-bromo-2-methoxy-phenyl)-N-{2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethyl}-acrylamide

HRID 854609Notes

Reaction equation

HRID 854609 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6](/[CH:8]=[CH:9]/[C:10]([OH:12])=O)[CH:7]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[F:46][C:47]1[CH:62]=[CH:61][C:50]([CH2:51][CH:52]2[CH2:57][CH2:56][N:55]([CH2:58][CH2:59][NH2:60])[CH2:54][CH2:53]2)=[CH:49][CH:48]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6](/[CH:8]=[CH:9]/[C:10]([NH:60][CH2:59][CH2:58][N:55]2[CH2:56][CH2:57][CH:52]([CH2:51][C:50]3[CH:49]=[CH:48][C:47]([F:46])=[CH:62][CH:61]=3)[CH2:53][CH2:54]2)=[O:12])[CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 676162trans-5-Bromo-2-methoxycinnamic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 179789732-[4-(4-Fluoro-benzyl)-piperidin-1-yl]-ethylamine

Product 1

HCID 10227358(E)-3-(5-bromo-2-methoxy-phenyl)-N-{2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethyl}-acrylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (E)-3-(5-bromo-2-methoxy-phenyl)-acrylic acid (0.072 g, 0.28 mmol) in DMF (10 ml) is treated with 2-(1H benzotriazol-1-yl)-1,1,3,3,-tetramethyluronium tetrafluoroborate (0.09 g, 0.28 mmol) and diisopropylethylamine (0.058 ml, 0.33 mmol). The resultant solution is added to 2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethylamine and the mixture stirred at RT for 18 hours. The solvents are evaporated and the crude residue purified by preparative HPLC to afford (E)-3-(5-bromo-2-methoxy-phenyl)-N-{2-[4-(4-fluoro-benzyl)-piperidin-1-yl]-ethyl}-acrylamide [MH]+ 475.2

Workup

  1. customThe solvents are evaporated
  2. customthe crude residue purified by preparative HPLC

Sources & evidence

ORD record
ord-d348a0b2925e42caa20546892169087d
Source dataset
uspto-grants-2007_08
Patent number
US07259173B2

Reaction notes

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