2-Methylbenzylamine → HCID 178424262, compound

HRID 1294711Notes

Reaction equation

HRID 1294711 reaction equation
[C:1]([N:3]=[C:4](OCC)[CH2:5][CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])#[N:2].[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21]>>[C:1]([N:3]=[C:4]([NH:21][CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[CH3:17])[CH2:5][CH:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])#[N:2]

Participants

3

Reactant 2

HCID 69932-MethylbenzylamineHCID 87820976HCID 87820976, compound

Product 1

HCID 178424262HCID 178424262, compound

Procedure

A mixture of Example 52C (0.1 g, 0.44 mmol) and 2-methylbenzylamine (0.2 mL) was heated to 90° C. for 2.5 hours. The mixture was cooled down to room temperature and purified by flash chromatography (eluting with 35% ethyl acetate/hexanes) to give the title compound as a white solid. MS (ESI/NH3) m/z 292 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.24-1.26 (d, 3H) 2.17 (s, 3H) 2.79-2.82 (d, 2H) 3.38-3.40 (m, 1H) 4.25-4.29 (m, 2H) 7.08-7.32 (m, 9H) 9.01 (t, 1H).

Workup

  1. custompurified by flash chromatography (eluting with 35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-500f828c6fa745d0960829c28a93ee7c
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

Loading…