Tryptamine → HCID 20035625, compound

HRID 1905415Notes

Reaction equation

HRID 1905415 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[C:13]([CH:21]([CH2:27][CH2:28][CH2:29]Cl)[C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.ClC1C=CC=CC=1>O>[C:14]1([C:13]2[N:1]([CH2:2][CH2:3][C:4]3[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[NH:6][CH:5]=3)[CH2:29][CH2:28][CH2:27][C:21]=2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1150TryptamineHCID 7964ChlorobenzeneHCID 54572410HCID 54572410, compound

Product 1

HCID 20035625HCID 20035625, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.273 g. (0.0017 mole) of tryptamine are added to a solution of 0.229 g. (0.00085 mole) of (±)-ethyl 2-benzoyl-5-chloro-valerate prepared according to Example 29 in 5 ml. of chlorobenzene, and the reaction mixture is heated on an oil bath of 150° C. for 5 hours, with stirring, while the water formed is allowed to distill off slowly together with chlorobenzene. After cooling the precipitate is filtered off, washed with chlorobenzene, and the combined chlorobenzene solution is evaporated from a bath of 40° C. on a rotating evaporator. The title compound is obtained by subjecting the residue to column chromatography on 40 g. of silica gel (Geduran Si 60, 0.063-0.200 mm.) using toluene containing 10% of diethyl amine as an eluting agent.

Workup

  1. customformed
  2. distillationto distill off slowly together with chlorobenzene
  3. temperatureAfter cooling the precipitate
  4. filtrationis filtered off
  5. washwashed with chlorobenzene
  6. customthe combined chlorobenzene solution is evaporated from a bath of 40° C. on a rotating evaporator

Sources & evidence

ORD record
ord-86466b9da2484be689c0fbccbea7f48e
Source dataset
uspto-grants-1989_06
Patent number
US04843080

Reaction notes

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