Hydrochloric Acid → HCID 20066013, compound

HRID 359066Notes

Reaction equation

HRID 359066 reaction equation
[CH3:1][N:2]([CH2:34][C:35]#[CH:36])[C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14](CC2C=CC=CC=2)[CH2:15][CH:16]([OH:25])[CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:7]=1.[ClH:37]>CC(O)C.[Pd].ClCCl.CCOCC>[ClH:37].[CH3:1][N:2]([CH2:34][C:35]#[CH:36])[C:3](=[O:33])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][NH:14][CH2:15][CH:16]([OH:25])[CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:10][CH:11]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 23127016HCID 23127016, compound

Product 1

HCID 20066013HCID 20066013, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-methy-N-propargyl 4-[2-(N-benzyl-N-(2-hydroxy-3phenoxypropyl)amino)ethyl]phenoxyacetamide (1.0 g) was dissolved in propan-2-ol (70 ml). 10% Palladium on carbon catalyst (0.2 g) was added and the mixture hydrogenated overnight under an atmosphere of hydrogen. The catalyst was separated by filtration through Keiselguhr and the filtrate evaporated under reduced pressure to give an oil. This residue was dissolved in dichloromethane (70 ml) and the pH (as indicated on moist test paper) was adjusted to 3 by adding a saturated solution of HCl in ether. The solvent was evaporated and this process was repeated as described in Example 26. The final residual oil (0.9 g) was suspended in a minimum amount of propan-2-ol from which it crystallised. A small amount of methyl acetate was added before the solid was filtered off and air-dried to give N-methyl-N-propargyl-4-[2-(2-hydroxy-3-phenoxypropylamino)ethyl]-phenoxyacetamide hydrochloride salt (0.3 g) mp 105°-107° C.. NMR: 0.73-0.92[m,3 H, hindered rotamers CH2CH3 ]; 1.35-1.67[m,2H, hindered rotamers, NCH2CH2CH3 ]; 2.80 and 2.96[pr.s,3H, hindered rotamers, N-CH3 ]; 2.84-3.02[m,2H,CHHD 2C6H4 ]; 3.02-3.30[m,4H,CH2NHCHHD 2]; 3.98[m,2H, OCH2CHOH]; 4.20[m,1H,CHOH]; 4.74[s,2H,OCH2CO]; 6.80-6.98[m,5H, aromatic H]; 7.10-7.34[m,4H, aromatic H].

Workup

  1. customthe mixture hydrogenated overnight
  2. customThe catalyst was separated by filtration through Keiselguhr
  3. customthe filtrate evaporated under reduced pressure
  4. customto give an oil
  5. customThe solvent was evaporated
  6. customcrystallised
  7. additionA small amount of methyl acetate was added before the solid
  8. filtrationwas filtered off
  9. customair-dried

Sources & evidence

ORD record
ord-ce351d6ed06d49fdbdcffda5877d6c02
Source dataset
uspto-grants-1991_03
Patent number
US04999377

Reaction notes

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