p-Chlorophenacyl bromide → 6-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine

HRID 1793175Notes

Reaction equation

HRID 1793175 reaction equation
[CH2:1]([C:8]1[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]1[C:20]([C:21]([CH2:23]Br)=O)=[CH:19][CH:18]=[C:17]([Cl:25])[CH:16]=1>>[Cl:25][C:17]1[CH:18]=[CH:19][C:20]([C:21]2[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:8]3[N:9]([CH2:10][C:11]([CH3:14])([CH3:13])[CH2:12]3)[CH:23]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 68303p-Chlorophenacyl bromideHCID 99205805-Benzyl-3,3-dimethyl-3,4-dihydro-2H-pyrrole

Product 1

HCID 99450016-(4-Chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine

Procedure

The 2-benzyl-4,4-dimethyl-1-pyrroline of the formula III is then cyclized with ω-bromo-4-chloroacetophenone to give the 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine of the formula II. The reaction is known from the prior art mentioned at the outset. ω-Bromo-4-chloroacetophenone can be obtained, for example, as described in Bull. Soc. Chim. Fr. 21, 69 (1899).

Sources & evidence

ORD record
ord-6ab0c792e2884cc19df6d6ecb4a193da
Source dataset
uspto-grants-2006_07
Patent number
US07078535B2

Reaction notes

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