Ammonia → HCID 19696130, compound

HRID 863534Notes

Reaction equation

HRID 863534 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH:12]([C:14]([OH:16])=O)[CH2:11][CH2:10][N:5]12.C([N:19](CC)CC)C.ClC(OCC)=O.N>O.CC(C)=O>[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH:12]([C:14]([NH2:19])=[O:16])[CH2:11][CH2:10][N:5]12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14954050HCID 14954050, compound

Product 1

HCID 19696130HCID 19696130, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A stirred suspension of 27 g (126 mmol) of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxylic acid in 30 ml of water and 450 ml of acetone was cooled to 0° C. and treated in succession with 14.7 g (145 mmol) of triethylamine and 17.3 g (159 mmol) of ethyl chloroformate. After 0.5 hour, 6.3 ml of 0.880 ammonia was added and stirring was continued for 1 hour. The solvent was removed under reduced pressure and the residue was triturated with aqueous ethanol. The product was filtered off and dried to give 13 g of 6,7,8,9-tetrahydropyrido[1,2-a]indole-8-carboxamide, as a white solid of melting point 165°-168° C.

Workup

  1. waitwas continued for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was triturated with aqueous ethanol
  4. filtrationThe product was filtered off
  5. customdried

Sources & evidence

ORD record
ord-abadb3f6839041e69040f076543a0afb
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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