Phenacyl bromide → HCID 21892156, compound

HRID 720397Notes

Reaction equation

HRID 720397 reaction equation
[Br-].[CH2:2]([N+:11]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[CH:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].BrCC(C1C=CC=CC=1)=O.[N:31]1C2CCCCC=2[CH:34]=[CH:33][CH:32]=1>C(#N)C>[C:3]([C:2]1[N:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[CH:14]=[CH:13][C:12]2=[C:33]([C:32]#[N:31])[CH:34]=1)(=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 663355,6,7,8-TetrahydroquinolineHCID 13530044HCID 13530044, compound

Product 1

HCID 21892156HCID 21892156, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Phenacyl)-5,6,7,8-tetrahydro-quinolinium bromide: The title compound was prepared from 2-bromo-1-phenyl-ethanone (507.7 mg, 2.55 mmol), 5,6,7,8-tetrahydro-quinoline (275 μL, 2.13 mmol) and acetonitrile (4.2 mL), similar to Example 1a, and yielded 694 mg (98%) as a light tan solid. 1H NMR (DMSO-d6): 8.80 (d, J=6.05 Hz, 1H), 8.45 (d, J=7.70 Hz, 1H), 8.11 (d, J=7.97 Hz, 2H), 8.00 (dd, J=7.69, 6.31 Hz, 1H), 7.82 (t, J=7.42 Hz, 1H), 7.68 (t, J=7.56 Hz, 1H), 6.52 (s, 2H), 3.02 (t, J=6.18 Hz, 2H), 2.92 (t, J=6.18 Hz, 2H), 1.85 (m, 2H), 1.77 (m, 2H).

Workup

  1. customyielded 694 mg (98%) as a light tan solid

Sources & evidence

ORD record
ord-b833b566ba614368a348aa96f9843ed0
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

Loading…