Ammonia → 1-(3-Chlorobenzylamino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

HRID 396220Notes

Reaction equation

HRID 396220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:13][N:12]=1.N>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:6][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH2:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 77802Benzenemethanamine, 3-chloro-HCID 111611391-Chloro-4-(pyridin-4-ylmethyl)-isoquinoline

Product 1

HCID 230036251-(3-Chlorobenzylamino)-4-[(pyridin-4-yl)-methyl]-isoquinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

With the exclusion of moisture, 1.6 ml (13.1 mmol) of 3-chlorobenzylamine and 800 mg (3.14 mmol) of 1-chloro-4-(pyridin-4-ylmethyl)-isoquinoline (Example 1e) are stirred for 2 hours at 150° C. The mixture is suspended in ethyl acetate, 1 ml of concentrated ammonia solution is added, washing with water and brine is carried out, and the organic phase is dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; ethyl acetate) yields the title compound: m.p. 141-142° C.; 1H NMR (DMSO-d6) 8.39 (d, 2H), 8.31 (d, 1H), 8.03 (t, HN), 7.82 (s, 1H), 7.69 (d, 1H), 7.61 (t, 1H), 7.50 (t, 1H), 7.40 (s, 1H), 7.33 (m, 2H), 7.26 (m, 1H), 7.20 (d, 2H), 4.73 (d, 2H), 4.14 (s, 2H); FAB-MS: (M+H)+=360; Anal. calc. (C22H18N3Cl) C 73.43%, H 5.04%, N 11.68%, Cl 9.85%; found C 73.2%, H 5.1%, N 11.6%, Cl 9.9%.

Workup

  1. washwashing with water and brine
  2. dry with materialthe organic phase is dried (Na2SO4)
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9263aabc8d914e4eb3c051abd82987b8
Source dataset
uspto-grants-2003_08
Patent number
US06608071B2

Reaction notes

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