Triethylamine → N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-butanamide

HRID 1660335Notes

Reaction equation

HRID 1660335 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH3:7][C:8]1([CH2:21][NH2:22])[C:13]2[NH:14][C:15]3[C:20]([C:12]=2[CH2:11][CH2:10][O:9]1)=[CH:19][CH:18]=[CH:17][CH:16]=3.C(N(CC)CC)C>O1CCCC1>[CH3:7][C:8]1([CH2:21][NH:22][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[C:13]2[NH:14][C:15]3[C:20]([C:12]=2[CH2:11][CH2:10][O:9]1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 127081811,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-methanamine

Product 1

HCID 12708191N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-butanamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butanoyl chloride (5.3 g) is added to stirring mixture at 0° C. of 1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine (10.0 g, described in Example 3), triethylamine (5 g) and dry tetrahydrofuran (400 ml). The temperature is allowed to rise to room temperature, the reaction mixture is filtered, and the filtrate is evaporated to give the title compound (12.5 g): ir(CHCl3) 3420, 3250, 2885 and 1660 cm-1 ; nmr(CDCl3) δ 0.75 (t), 1.57 (s), 1.62 (m), 2.08 (t), 2.87 (m), 3.91 (t), 4.10 (t), 6.12 (s), 7.0-7.7 (m) and 9.86 (s).

Workup

  1. customto rise to room temperature
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-a71d81bd8e8544c8a4e7e1e4a4e7017e
Source dataset
uspto-grants-1981_12
Patent number
US04307234

Reaction notes

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