2-[(3,4-Dimethylphenyl)oxy]acetaldehyde → 8-(3,4-Dimethylphenoxymethyl)-3-ethyl-1-iodo-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine

HRID 1929673Notes

Reaction equation

HRID 1929673 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[C:6]([I:8])[N:7]=1)[CH3:2].[CH3:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[O:16][CH2:17][CH:18]=O>>[CH3:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[O:16][CH2:17][CH:18]1[NH:11][CH2:10][CH2:9][N:4]2[C:3]([CH2:1][CH3:2])=[N:7][C:6]([I:8])=[C:5]12

Participants

3

Reactant 2

HCID 148160142-[(3,4-Dimethylphenyl)oxy]acetaldehydeHCID 66734063HCID 66734063, compound

Product 1

HCID 667366848-(3,4-Dimethylphenoxymethyl)-3-ethyl-1-iodo-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine

Procedure

According to the general procedure (GP10), microwave-assisted Pictet-Spengler reaction (60 W; 140° C.; 6.5 bars; 10 min.) between 2-(2-ethyl-4-iodo-imidazol-1-yl)-ethylamine (6.000 mmol) and (3,4-dimethyl-phenoxy)-acetaldehyde (0.985 g; 6.000 mmol) afforded 8-(3,4-dimethyl-phenoxymethyl)-3-ethyl-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.70 min.; [M+H]+=412.12 g/mol.

Sources & evidence

ORD record
ord-f0817317ffce40b290b1b6c7a21fc83d
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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