Dimethylformamide → HCID 19854821, compound

HRID 1649797Notes

Reaction equation

HRID 1649797 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=1.C([N:34]([CH2:38]C)C(C)C)(C)C.C[N:41](C)C=O>>[NH2:41][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([CH:9]([CH2:38][NH:34][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][N:23]=2)[OH:10])=[CH:5][C:6]=1[Cl:8]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 432363,5-Dichlorobenzylic alcoholHCID 81531DiisopropylethylamineHCID 198547802-[3-[(6-Bromohexyl)oxy]propyl]-5-nitropyridine

Product 1

HCID 19854821HCID 19854821, compound

Procedure

A solution of 4-amino-α-aminomethyl)-3,5-dichlorobenzenemethanol (361 mg), 2-[3-[(6-bromohexyl)oxy]propyl]-5-nitropyridine (378 mg) and N,N-diisopropylethylamine (168 mg) in dimethylformamide (5 ml) was stirred at 100° for 3 h. The solvent was evaporated in vacuo to give an oil. Purification by FCC eluting with System A (95:5:1) gave the title compound as a yellow solid (250 mg), m.p. 60°-61°.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give an oil
  3. customPurification by FCC
  4. washeluting with System A (95:5:1)

Sources & evidence

ORD record
ord-2dc9fcb3c0cb4191bb6ab246333ff52d
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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