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Dimethylformamide → Undecylamine

HRID 535115
Notes
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Reaction equation

HRID 535115 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](O)=O.C(N(CC)CC)C.C1C(SSC2C=CC([N+]([O-])=O)=C(C(O)=O)C=2)=CC(C(O)=O)=C([N+]([O-])=O)C=1.CN(C=O)C>O1CCCC1>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 62545,5'-Dithiobis(2-nitrobenzoic Acid)HCID 8471TriethylamineHCID 1708311-Aminoundecanoic acid

Product 1

HCID 81742Undecylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
2×

Procedure

In this example, the spacer unit is 11-amino-undecanoic acid. The spacer (411 mg, 2.04 mmol, 4 eq) is suspended in a dry organic solvent, for example tetrahydrofuran (THF). Depending on its solubility and the stability of the Raman marker unit, the suspension temperature can be varied between −78° C. and reflux. First, an auxiliary base (2.1 ml triethylamine) is added. Then, the activated marker unit in a suitable organic solvent, for example DTNB-NHS (300 mg, 0.51 mmol in 10 ml THF and 5 ml DMF), is added dropwise. Depending on the reactivity, the reaction mixture is stirred 10 to 48 h, in this case 16 h. The solvent is removed by vacuum, the remaining solid is washed with NaHSO4 solution and a suitable organic solvent. Further purification can be achieved by column chromatography, preferably on reversed phase silica (yield: 260 mg, 0.34 mmol, 67%).

Workup

  1. customcan be varied between −78° C.
  2. temperaturereflux
  3. customThe solvent is removed by vacuum
  4. washthe remaining solid is washed with NaHSO4 solution
  5. customFurther purification

Sources & evidence

ORD record
ord-23394465a7ce451786c3fbf93ef3ead9
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08854617B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes