Tryptamine → HCID 23366813, compound

HRID 1079377Notes

Reaction equation

HRID 1079377 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[F:13][C:14]([F:24])([F:23])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1.C1COCC1.NCC[C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1>C(Cl)Cl.C(OC(=O)C)C.CCCCCC>[F:13][C:14]([F:23])([F:24])[C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:20][C:1]([NH:8][CH2:12][CH2:11][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[NH:35][CH:34]=2)=[O:2])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 1150TryptamineHCID 8028TetrahydrofuranHCID 676844-(Trifluoromethyl)benzenemethanol2×HCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 23366813HCID 23366813, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1,1'-carbonyldiimidazole (2.03 g, 12.5 mmol), p-trifluoromethylbenzyl alcohol (2.2 g, 12.5 mmol) and THF (100 mL) was stirred for 2 hours. The reaction was monitored by TLC (silica gel, hexane:ethylacetate; 2:1) to examine the complete disappearence of p-trifluoromethylbenzyl alcohol. To this solution, 2.0 g (12.5 mmol) of tryptamine was added and the mixture was stirred overnight. The reaction contents were diluted with methylene chloride (100 mL). The organic layer was washed with 5% 3×100 mL of HCl, water (3×100 mL) and dried over anhydrous MgSO4. Upon evaporation of the solvent, under vacuum, crude N-(para-Trifluoromethylbenzyloxycarbonyl)tryptamine was obtained as a solid which was crystallized from ether-hexane mixture (2.6 g, 57% yield). mp 92°-94° C.

Workup

  1. customThe reaction contents
  2. washThe organic layer was washed with 5% 3×100 mL of HCl, water (3×100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. customUpon evaporation of the solvent

Sources & evidence

ORD record
ord-c0f98464b0704c4e8ddbce0f27798b5c
Source dataset
uspto-grants-1996_12
Patent number
US05580878

Reaction notes

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