Iodine → HCID 544889, compound

HRID 1719520Notes

Reaction equation

HRID 1719520 reaction equation
CO.II.OC1C=CC=CC=1CC1(NCC2C=CC=CC=2)CCCCC1.[C:27]([C:35]1[CH2:40][CH2:39][CH2:38][CH2:37][C:36]=1[NH:41]CC1C=CC=CC=1)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[Pd].C(Cl)Cl>[OH:34][CH:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]1[NH2:41]

Participants

7

Reactant 4

HCID 807IodineHCID 887MethanolHCID 319570[2-(Benzylamino)cyclohex-1-en-1-yl](phenyl)methanone2×HCID 20211919HCID 20211919, compound

Product 1

HCID 544889HCID 544889, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A 17.9 kg lot of N-[2-(benzoyl)-cyclohexen-1-yl]benzylamine in ethanol solution from Step B above, was hydrogenated at 100 psig over 10% palladium on carbon (1800 g) in a 20 or 30 gallon autoclave. The reduction required 18 days for completion. The hydrogenation reaction was monitored periodically by thin layer chromatography (tlc) analyses using alumina GF plates (Analtech) and 5% methanol in methylene chloride. The plates were visualized with iodine. The reduction proceeds through the intermediate N-[[2(hydroxy)phenylmethyl]cyclohexyl]benzylamine which was evident by the tlc methods.

Workup

  1. custom18 days
  2. customThe hydrogenation reaction

Sources & evidence

ORD record
ord-59f553b4b7984401bad747bb7753f656
Source dataset
uspto-grants-1985_09
Patent number
US04540690

Reaction notes

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