Citronellal → HCID 20398738, compound

HRID 1981453Notes

Reaction equation

HRID 1981453 reaction equation
[C:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.C1(N)C2C(=CC=CC=2)C=CC=1.[CH3:24][C:25](=[CH:27][CH2:28][CH2:29][CH:30]([CH2:32][CH:33]=O)[CH3:31])[CH3:26].C([BH3-])#N.[Na+]>CO>[CH2:33]([NH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[CH2:32][CH:30]([CH2:29][CH2:28][CH:27]=[C:25]([CH3:26])[CH3:24])[CH3:31]

Participants

6

Reactant 4

HCID 7794CitronellalHCID 86401-NaphthylamineHCID 110941-Naphthalenamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydride

Product 1

HCID 20398738HCID 20398738, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.0 g α-naphthylamine (14 mmol) and 0.01 gm α-naphthylamine-HCl were added to 25 ml absolute methanol along with 2.15 gm citronellal (14 mmol) and stirred for five minutes, after which the solution turned hazy. Then 0.53 gm (8.4 mmol) sodium cyanoborohydride was added and a brief exotherm occurred. The mixture was stirred overnight at room temperature. The bottom organic layer was separated from the top aqueous layer. An IR spectra of the organic layer (a brown oil) showed no carbonyl group and very little absorption in the OH/NH region (330-360 nm). Upon vacuum distillation of the organic layer the component having a bp of 175°-180° C. was collected. The desired product was recovered as a pale yellow oil in 21% yield. The structure of the amine product was confirmed by NMR.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customThe bottom organic layer was separated from the top aqueous layer
  3. customno carbonyl group and very little absorption in the OH/NH region (330-360 nm)
  4. distillationUpon vacuum distillation of the organic layer the component
  5. customwas collected
  6. customThe desired product was recovered as a pale yellow oil in 21% yield

Sources & evidence

ORD record
ord-fdbc269b5b124f07b7ae5a7fb9923a9b
Source dataset
uspto-grants-1985_04
Patent number
US04514045

Reaction notes

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