Dimethylamine → Indole, 5-bromo-3-(dimethylamino)methyl-

HRID 330277

Reaction equation

[CH2:1]=O.[CH3:3][NH:4][CH3:5].O.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2>O1CCOCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:5](=[CH:15][CH:16]=1)[NH:4][CH:3]=[C:11]2[CH2:12][N:13]([CH3:1])[CH3:14]

Participants

Conditions

Temperature: 5 °C

Procedure

According to A. Ek, et al., J Am. Chem. Soc., 76, 5579 (1954), to an ice-cooled mixture of dioxane (130 mL) acetic acid (130 mL) , 37% aqueous formaldehyde (9.9 mL, 0.133 mol), 40% aqueous dimethylamine (17.6 mL, 0.140 mol), and H2O (10.6 mL) was added a solution of 5-bromoindole (25.0 g, 0.128 mol) in dioxane (130 mL) over 35 minutes. The internal temperature was maintained at 5° C. during the addition. After 2 hours, the cooling bath was removed and stirring was continued at room temperature overnight. The mixture was diluted with H2O (1600 mL), charcoal and celite were added and the mixture was filtered. 2.5 N NaOH (1000 mL) was added and the resulting precipitate was collected by filtration to yield 98% of product as a white solid.

Workup

customthe cooling bath was removed
waitwas continued at room temperature overnight
additionThe mixture was diluted with H2O (1600 mL), charcoal and celite
additionwere added
filtrationthe mixture was filtered
addition2.5 N NaOH (1000 mL) was added
filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record: ord-a5947a28d4e94a49948e1b5ae2bf71f0
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04895860

Linked notes

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