Hydrochloric Acid → HCID 15544537, compound

HRID 1883948Notes

Reaction equation

HRID 1883948 reaction equation
P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.Br[C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21]([C:23]([NH2:25])=[O:24])=[CH:20][C:19]=2[CH:26]=1.[CH2:27]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>C1(C)C(C)=CC=CC=1>[CH2:27]([N:34]1[CH2:39][CH2:38][N:37]([C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21]([C:23]([NH2:25])=[O:24])=[CH:20][C:19]=3[CH:26]=2)[CH2:36][CH2:35]1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 759941-BenzylpiperazineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 25026635-Bromobenzofuran-2-carboxamide

Product 1

HCID 15544537HCID 15544537, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
125 °C

Procedure

0.30 g of P(t-Bu)3, 4.5 g of 5-bromobenzofuran-2-carboxamide, 4.9 g of benzylpiperazine and 5.0 g of Na t-OBu are added to a suspension of 0.085 g of Pd(II) acetate in 150 ml of xylene after the latter has been stirred for 15 minutes, and the mixture is warmed at 125° C. for 12-18 hours under the protective gas nitrogen. After cooling, the mixture is added to 500 ml of 2N hydrochloric acid, and the aqueous phase is extracted 3 times with 200 ml of ethyl acetate. The aqueous phase is adjusted to pH 10 using aqueous NaOH (20%) with pH and temperature monitoring (20-25° C.), and the 5-(4-benzyl-1-piperazinyl)benzofuran-2-carboxamide produced as a solid is filtered off and crystallized, for example, from ethanol/water (product weight: 4.0 g/64%/m.p. 277-279°).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase is extracted 3 times with 200 ml of ethyl acetate
  3. customwith pH and temperature monitoring (20-25° C.)

Sources & evidence

ORD record
ord-0e2b074c92cf457fb9854a54d883eb86
Source dataset
uspto-grants-2004_07
Patent number
US06762300B2

Reaction notes

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