Triethylamine → HCID 20216108, compound

HRID 236557Notes

Reaction equation

HRID 236557 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:19][CH:18]=[CH:17][CH2:16][CH2:15]2)=[CH:11][CH:10]=1.[Cl:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(Cl)Cl>[ClH:22].[CH2:26]([O:25][C:23]([O:8][C:9]1[CH:21]=[CH:20][C:12]([CH2:13][N:14]2[CH2:15][CH:16]=[CH:17][CH2:18][CH2:19]2)=[CH:11][CH:10]=1)=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 202160941-(4-Hydroxybenzyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 20216108HCID 20216108, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Triethylamine (1.2 g.) was added with stirring to a solution of 1-(4-hydroxybenzyl)-1,2,3,6-tetrahydropyridine (1.9 g.) in methylene chloride (30 ml.) at 0° C. Ethyl chloroformate (1.2 g.) was then added dropwise and the mixture stirred at 25° C. for 16 hours and then evaporated. Water (30 ml.) was added to the residue and the mixture was extracted with ether (2×30 ml.). The combined extracts were dried (MgSO4) and evaporated. The residue was dissolved in acetone (20 ml.) and acidified with ethereal hydrogen chloride to give 1-[4-(ethoxycarbonyloxy)benzyl]-1,2,3,6-tetrahydropyridine hydrochloride (1.5 g.) m.p. 168°-172° C. (after recrystallisation from ethanol-ethyl acetate).

Workup

  1. customevaporated
  2. additionWater (30 ml.) was added to the residue
  3. extractionthe mixture was extracted with ether (2×30 ml.)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in acetone (20 ml.)

Sources & evidence

ORD record
ord-81b3b030870149c6b3e9f3ef5adcf177
Source dataset
uspto-grants-1987_02
Patent number
US04645771

Reaction notes

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