4-(Dimethylamino)Benzaldehyde → n-(5-Carboxypentyl)-4-(4-(dimethylamino)styryl)pyridinium bromide

HRID 1517159Notes

Reaction equation

[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][CH:5]=1)[CH3:3].[Br-:12].[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N+:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1C)([OH:15])=[O:14].N1CCCC[CH2:29]1>C(O)C>[Br-:12].[C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N+:21]1[CH:22]=[CH:23][C:24]([CH:29]=[CH:10][C:7]2[CH:6]=[CH:5][C:4]([N:2]([CH3:1])[CH3:3])=[CH:9][CH:8]=2)=[CH:25][CH:26]=1)([OH:15])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-N,N-dimethylaminobenzaldehyde (3 g, 20 mmoles), N-(5-carboxypentyl)picolinium bromide (5.6 g, 20 mmoles) and piperidine (2 mL) in ethanol (100 mL) was heated at 60° C. overnight. The mixture was evaporated to dryness in vacuo. The residue was redissolved in methanol and then precipitated with ether to give the title product (6.7 g).

Workup

customThe mixture was evaporated to dryness in vacuo
dissolutionThe residue was redissolved in methanol
customprecipitated with ether

Sources & evidence

ORD record: ord-39c4159d511f4246b2c94c9d16179661
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232050B2

Reaction notes

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