Camphor → HCID 20398731, compound

HRID 1981454Notes

Reaction equation

HRID 1981454 reaction equation
[C:1]12([CH3:11])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=O.[C:12]1([NH2:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.Cl.C1(N)C2C(=CC=CC=2)C=CC=1.C([BH3-])#N.[Na+]>CO>[C:1]12([CH3:11])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:2]2[NH:22][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 2537CamphorHCID 86401-NaphthylamineHCID 110941-Naphthalenamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydride

Product 1

HCID 20398731HCID 20398731, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Camphor (10 gm), 9.4 gm α-naphthylamine, 0.1 gm α-naphthylamine-HCl and 30 gm 1 Å molecular sieves were added to 40 ml anhydrous methanol. Sodium cyanoborohydride (2.5 gm) was added dropwise and stirred under N2 for 48 hours. The sieves were removed by filtration and 5 drops of concentrated HCl were added to the filtrate until it was acidic (pH>7). The solvent was stripped by boiling and 10 gm potassium hydroxide was added to the remaining mixture. The aqueous phase was extracted with ether over potassium carbonate. The extractions were filtered to remove the potassium carbonate. After the ether was evaporated, the mixture was distilled under high vacuum. The material boiling at 120° C. and 0.1 mm of mercury was collected. IR spectra verified that this material was the product.

Workup

  1. customThe sieves were removed by filtration and 5 drops of concentrated HCl
  2. additionwere added to the filtrate until it
  3. addition10 gm potassium hydroxide was added to the remaining mixture
  4. extractionThe aqueous phase was extracted with ether over potassium carbonate
  5. extractionThe extractions
  6. filtrationwere filtered
  7. customto remove the potassium carbonate
  8. customAfter the ether was evaporated
  9. distillationthe mixture was distilled under high vacuum
  10. customThe material boiling at 120° C. and 0.1 mm of mercury was collected

Sources & evidence

ORD record
ord-c163564027564cc6bfe4f6a91ecfcfdb
Source dataset
uspto-grants-1985_04
Patent number
US04514045

Reaction notes

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