Hydrochloric Acid → HCID 20298131, compound

HRID 1389161Notes

Reaction equation

HRID 1389161 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C:17]([OH:19])=O)[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH2:21]([N:28]1CCC(OCC(OC)=O)CC1)[C:22]1C=CC=CC=1.C(N)C>CO>[CH2:21]([NH:28][C:17](=[O:19])[CH2:16][O:15][CH:12]1[CH2:11][CH2:10][N:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:14][CH2:13]1)[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 20298108HCID 20298108, compoundHCID 70050009HCID 70050009, compound

Product 1

HCID 20298131HCID 20298131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1-Benzylpiperidin-4-oxy)acetic acid, hydrochloride, prepared similarly to Preparation L Part A, was converted to its methyl ester by refluxing in methanol plus concentrated hydrochloric acid. Methyl 2-(1-benzylpiperidin-4-oxy)acetate (10 g) and ethylamine (50 ml) with 3 A molecular sieves were heated in a bomb at 120° for 6 hours. The solvent was then evaporated in vacuo, the residue triturated with ether, filtered and the filtrate evaporated to give N-ethyl-2-(1-benzylpiperidin-4-oxy)acetamide (7.7 g) as an oil. This product (7.0 g) in ethanol (150 ml) was hydrogenated over 5% palladium on charcoal (Engelhardt special debenzylation catalyst) at 50° and 50 p.s.i.

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue triturated with ether
  3. filtrationfiltered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-016f43734f9b49b6a119919081691ae4
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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