Triethylamine → HCID 68494193, compound

HRID 1944216Notes

Reaction equation

HRID 1944216 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH:15]([CH3:21])[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:27]Cl.C(N(CC)CC)C>CCO>[CH3:35][O:34][C:30]1[CH:29]=[C:26]([CH:25]=[C:24]([O:23][CH3:22])[C:31]=1[O:32][CH3:33])[CH2:27][N:14]1[CH2:13][CH2:12][C:11]2[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH:15]1[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 6226266-(Benzyloxy)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 68494193HCID 68494193, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 250 (170 mg, 0.6 mmol), 3,4,5-trimethoxybenzyl chloride (156 mg, 0.72 mmol) and triethyl amine (0.17 ml, 1.2 mmol) in EtOH (3 ml) was heated in the microwave at 130° C. for 1.5 h, then at 170° C. for 30 min. The reaction mixture was concentrated in vacuo. Purification (flashmaster: 20 g, gradient elution 100% hex to 50% hex:50% EtOAc over 25 min) afforded The title compound (58 mg, 21%) as a colourless oil. 1H NMR (270 MHz; CDCl3) 1.36 (3H, d, J=6.7 Hz, CH3CH), 2.47-2.55 (1H, m, one of CH2), 2.67-2.84 (2H, m, 2×CH, CH2), 2.98-3.07 (1H, m, one of CH2), 3.59-3.73 (2H, m, CH2), 3.83 (9H, s, 3×OCH3), 3.88 (3H, s, OCH3), 5.09 (2H, s, CH2), 6.56-6.62 (4H, m, 4×CH), 7.27-7.44 (5H, m, 5×CH, phenyl). LC/MS (ES+) tr=1.26 min, m/z 464.34 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customPurification (flashmaster: 20 g, gradient elution 100% hex to 50% hex:50% EtOAc over 25 min)

Sources & evidence

ORD record
ord-95f4000f2a4f478a85c26b1fe2759a1c
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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