4-Bromoaniline → HCID 69100733, compound

HRID 2115046Notes

Reaction equation

HRID 2115046 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13](=[O:17])[C:14]([OH:16])=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[Br:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:14](=[O:16])[C:13]([N:10]2[CH2:9][CH2:8][CH:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[O:17])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51342220[4-(4-Fluorobenzyl)piperidin-1-yl](oxo)acetic acid

Product 1

HCID 69100733HCID 69100733, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.64 g (2.4 mmol) of [4-(4-fluoro-benzyl)piperidin-1-yl]-oxo-acetic acid, 0.34 ml (2.4 mmol) of triethylamine, 0.35 g (2 mmol) of 4-bromo-aniline (Aldrich), 0.91 g (2.4 mmol) of HBTU and 10 ml of dimethylformamide is stirred at room temperature for 24 hours. The reaction mixture is concentrated. Then 30 ml of 8% sodium hydrogencarbonate solution and 30 ml of chloroform is added to the mixture. The organic layer is separated and the water phase is extracted three times with 20 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated. The residue is treated with diethylether and the crystals are filtered off to yield 0.36 g (43%) of the title compound. Melting Point: 156-158° C. (diethylether)

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additionThen 30 ml of 8% sodium hydrogencarbonate solution and 30 ml of chloroform is added to the mixture
  3. customThe organic layer is separated
  4. extractionthe water phase is extracted three times with 20 ml of chloroform
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. concentrationconcentrated
  7. additionThe residue is treated with diethylether
  8. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-277298065ed74cd28267f864f4ac22de
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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