Triethylamine → (E)-3-(4'-chlorobiphenyl-4-yl)-N-(4-piperidin-1-ylmethylphenyl)acrylamide

HRID 898618Notes

Reaction equation

HRID 898618 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N:19]1([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11](/[CH:14]=[CH:15]/[C:16]([NH:32][C:29]3[CH:28]=[CH:27][C:26]([CH2:25][N:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:31][CH:30]=3)=[O:18])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 8461504-(Piperidin-1-ylmethyl)anilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 5957595HCID 5957595, compound

Product 1

HCID 9980157(E)-3-(4'-chlorobiphenyl-4-yl)-N-(4-piperidin-1-ylmethylphenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.544 g (2.103 mmol) (E)-3-(4′-chloro-biphenyl-4-yl)-acrylic acid, 0.440 g (2.313 mmol) 4-piperidin-1-ylmethyl-phenylamine, 0.736 g (2.313 mmol) TBTU, 0.313 g (2.313 mmol) HOBt and 1.025 mL (7.361 mmol) triethylamine in 10 mL DMF was stirred for 3 h at RT and then poured onto ice water and a little EtOAc. The precipitate was filtered off, washed with water and dried at 80° C. i. vac.

Workup

  1. additionpoured onto ice water
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried at 80° C. i

Sources & evidence

ORD record
ord-44d316947eb543eaa4a23ce368b25b1a
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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