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

HRID 513969Notes

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-1a9ce10d512b48fca4791051b064a470
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102835B2

Reaction notes

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