Butylamine → HCID 53914725, compound

HRID 330191Notes

Reaction equation

HRID 330191 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:11]([OH:13])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.CN(C)CCCN=C=NCC.[CH2:26]([NH2:30])[CH2:27][CH2:28][CH3:29]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:26]([NH:30][C:11](=[O:13])[CH2:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 3

HCID 8007ButylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18399719(1H-Indol-5-yl)acetic acid

Product 1

HCID 53914725HCID 53914725, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of indole-5-acetic acid (2.0 g), 4-dimethylaminopyridine (1.5 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.4 g), and butylamine (1.2 ml) in methylene chloride was stirred under a nitrogen atmosphere for 18 hr. The reaction was diluted with methylene chloride, washed (10% (v/v) hydrochloric acid, water, brine), dried (MgSO4), and evaporated to give N-butylindole-5-acetamide (2.03 g, 77%) as an amber oil: NMR (300 MHz, CDCl3): 0.84(t, 3H, N(CH2)3CH3), 3.16(m, 2H, NCH2), 3.68(s, 2H, ArCH2), 5.44(br s, 1H, NH), 6.51(m, 1H, H2 -indole), 8.49(br s, 1H, NH).

Workup

  1. washwashed (10% (v/v) hydrochloric acid, water, brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-3395187c8c914a558417012821f8d2a8
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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