2-Bromopyridine → HCID 13787361, compound

HRID 2118678Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[CH2:13]([N:20]1[CH2:25][CH2:24][CH:23]([C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:26]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([OH:33])[CH:23]1[CH2:22][CH2:21][N:20]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:25][CH2:24]1

Participants

Conditions

Temperature: -65 °C

Procedure

2.1 ml (2.2 10-2 mole) of 2-bromopyridine in solution in 10 ml of tetrahydrofuran (THF) are added dropwise to a solution, cooled to -65° C., of 15.6 ml (2.5 10-2 mole) of n-BuLi and of 20 ml of THF. The mixture is stirred for 1/4 h at -65° C. and then 5.6 g (2 10-2 mole) of 1-benzyl-4-benzoylpiperidine in 20 ml of THF are added dropwise while the temperature is maintained at -65° C. The mixture is allowed to warm up very slowly and is then left overnight. It is heated to the reflux temperature for 2 h and then evaporated to dryness, and the residue is taken up with a mixture of water and ether. The ether phase is washed with water, dried, filtered and evaporated down. Chromatography on silica is carried out (eluent 95/5 CH2Cl2 /MeOH). A product which crystallizes from petroleum ether is collected. M.p.= 142°-143° C.

Workup

temperatureis maintained at -65° C
temperatureto warm up very slowly
temperatureIt is heated to the reflux temperature for 2 h
customevaporated to dryness
additionthe residue is taken up with a mixture of water and ether
washThe ether phase is washed with water
customdried
filtrationfiltered
customevaporated down
customA product which crystallizes from petroleum ether
customis collected

Sources & evidence

ORD record: ord-2b45b36dec6a4c7ba00154788bb42b47
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04680296

Reaction notes

Loading…