1-Chloro-4-(chloromethyl)benzene → HCID 22850905, compound

HRID 487109Notes

Reaction equation

HRID 487109 reaction equation
[CH2:1]1[C@@H:10]2[C@H:5]([CH2:6][CH2:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[CH2:4][NH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>CN(C=O)C>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:3]2[CH2:2][CH2:1][C@@H:10]3[C@H:5]([CH2:6][CH2:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=43)[CH2:4]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 54260071HCID 54260071, compound

Product 1

HCID 22850905HCID 22850905, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 3, step 4, 0.202 g (1.08 mmol) of crude trans-1,2,3,4,4a,5,6,10b-octahydro benz[f]isoquinoline in 10 ml of anhydrous DMF was reacted with 0.164 g (1.19 mmol) of anhydrous potassium carbonate and 0.183 g (1.14 mmol) of 4-chlorobenzyl chloride. Chromatography on flash silica, eluting with 30% ethyl acetate/petroleum ether, gave 0.110 g (33%) of the title product as a white solid. The hydrochloride salt was made using ethereal hydrogen chloride. Upon evaporation of the solvent the title product hydrochloride was obtained as a white solid, m.p. 257°-259° C. NMR δ(D2O/CD3CN) 1.51 (1H, m), 1.65 (1H, m), 1.78-1.82 (2H, m), 2.59-2.67 (2H, m), 2.80-2.89 (3H, m), 3.13 (1H, t of d), 3.41 (1H, m), 3.60 (1H, m), 4.29 (2H, d, J=3.7 Hz), 7.14-7.20 (3H, m), 7.25-7.28 (1H, m), 7.52 (4H, m). m/z (CI+, NH3) 312 (M+H)+, 186 (M-CH2C6H4Cl) +, 125. Analysis calcd. for C20H23Cl2N: C, 68.97; H, 6.66; N, 4.02%. Found: C, 68.59; H, 6.63; N, 3.98%.

Workup

  1. washChromatography on flash silica, eluting with 30% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e8bbf5ac99d94efbbd4937c779459bf8
Source dataset
uspto-grants-1994_03
Patent number
US05294618

Reaction notes

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