p-Bromochlorobenzene → HCID 9964563, compound

HRID 984690Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[NH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1

Participants

Reactant 2

HCID 7806p-Bromochlorobenzene

HCID 235274-(Aminomethyl)piperidine

Product 1

HCID 9964563HCID 9964563, compoundYield 60%

Procedure

Using the general procedure, 4-bromochlorobenzene (192 mg, 1.0 mmol) was coupled with 4-aminomethylpiperidine (171 mg, 1.5 mmol) at 100° C. for 20 h. Purification of the crude product by column chromatography on silica gel using methanol/dichloromethane (saturated with ammonia) (1:20) as eluent afforded the desired product as a light yellow solid (134 mg, 60% yield). Rf=0.3 (methanol/dichloromethane (saturated with ammonia)=1:20).

Workup

customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record: ord-33b251c98a8843299281faa4a5f0210e
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867298B2

Reaction notes

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