2,4-Dichloro-5-(chloromethyl)pyridine → 11-Acetyl-3,8-dichloro-11,12-dihydropyrido[3,4-c][1]benzazocine

HRID 2224344Notes

Reaction equation

HRID 2224344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH:12]=[CH2:13])[CH:3]=1.[Cl:14][C:15]1[CH:20]=[C:19](Cl)[C:18]([CH2:22]Cl)=[CH:17][N:16]=1.C(N1C2C=CC=CC=2C=CC2N=C(Cl)C(F)=CC=2C1)(=O)C>>[C:9]([N:8]1[C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH:12]=[CH:13][C:19]2[CH:20]=[C:15]([Cl:14])[N:16]=[CH:17][C:18]=2[CH2:22]1)(=[O:11])[CH3:10]

Participants

4

Reactant 3

HCID 27627282,4-Dichloro-5-(chloromethyl)pyridineHCID 59717611N-(4-chloro-2-vinyl-phenyl)-acetamideHCID 743934126-Acetyl-2-chloro-3-fluoro-5,6-dihydro-pyrido[3,2-c][1]benzazocine

Product 1

HCID 7236678211-Acetyl-3,8-dichloro-11,12-dihydropyrido[3,4-c][1]benzazocineYield 52%

Procedure

The title compound (67.6 mg, 52%) was prepared from 9B (80 mg, 0.41 mmol) and 41B (80 mg, 0.41 mmol) in two steps by a route analogous to that used for the preparation of 1D. HPLC Rt=2.886 min; LCMS Found: (M+H)+=319.

Sources & evidence

ORD record
ord-157fb17a9d5644609662bc3ac50e6347
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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