Tryptamine → HCID 23366826, compound

HRID 1653690Notes

Reaction equation

HRID 1653690 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[CH:13]1([CH2:16][OH:17])[CH2:15][CH2:14]1.CCCCCC.C(OC(=O)C)C.NCC[C:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH:34]=1>C1COCC1>[CH:13]1([CH2:16][O:17][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])[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 1150Tryptamine2×HCID 682631,1'-CarbonyldiimidazoleHCID 75644Cyclopropanemethanol2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 23366826HCID 23366826, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 11.7 g (69.3 mmol) of carbonyldiimidazole and 5.0 g (69.3 mmol) of cyclopropylmethanol in 150 mL of THF was stirred, under nitrogen and later at room temperature for 4-5 hours or the time until the TLC (silica gel; hexane-ethylacetate, 4:1) analysis indicated a complete disappearance of cyclopropylmethanol in the mixture. To this reaction mixture, a solution of tryptamine (11.12 g, 69.3 mmol) in THF (5 mL) was added and stirred overnight. The TLC analysis indicated a complete disappearence of tryptamine. The solvent was removed and the residue was redissolved in methylene chloride (450 mL), washed with 5% HCl (4×100 mL), water, dried over MgSO4, filtered. The filtrate was swirled with 50 g of silica gel, filtered and concentracted under vacuum. The solid was crystallized from hexane-methylene chloride to furnish 13.6 g of N-cyclopropylmethyloxycarbonyltryptamine (75% yield). mp 88°-90° C.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was redissolved in methylene chloride (450 mL)
  3. washwashed with 5% HCl (4×100 mL), water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. filtrationfiltered
  7. customThe solid was crystallized from hexane-methylene chloride

Sources & evidence

ORD record
ord-70055569ed2d4198993b1db44db0b2a6
Source dataset
uspto-grants-1995_04
Patent number
US05403851

Reaction notes

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