1-Butanol → HCID 22256597, compound

HRID 1611557Notes

Reaction equation

HRID 1611557 reaction equation
[ClH:1].C[C:3]1[CH:4]=[C:5]2[C:12](=[CH:13][CH:14]=1)[C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][NH:6]2.C(O[CH:18](OCC)[CH2:19][N:20]([CH3:22])[CH3:21])C.Cl.[CH2:27](O)CCC>>[ClH:1].[ClH:1].[CH3:27][C:14]1[CH:13]=[C:12]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:7]1[CH:18]([CH2:19][N:20]([CH3:22])[CH3:21])[NH:11][CH2:10][CH2:9][C:8]2=1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 77163(2,2-Diethoxyethyl)dimethylamineHCID 222565882-(6-Methyl-1H-indol-3-yl)ethan-1-amine--hydrogen chloride (1/1)

Product 1

HCID 22256597HCID 22256597, compoundYield 25%

Procedure

To a stirred suspension of 6-methyltryptamine hydrochloride (2.00 g, 9.5 mmole) and dimethylaminoacetaldehyde diethyl acetal (1.53 g, 9.5 mmole) in dry n-butanol (45 mL) at RT was added concentrated hydrochloric acid (1.6 mL, 19.0 mmole). The reaction solution was heated to reflux under an atmosphere of nitrogen. After 6 hr, the reaction solution was cooled to RT without stirring for 12 hr. The precipitate was filtered and then washed sequentially with n-butanol and diethyl ether. Drying under high vacuum afforded the title compound (0.74 g, 25%) as a light yellow solid: MS (ES) m/e 244 (M+H-2HCl)+.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. filtrationThe precipitate was filtered
  4. washwashed sequentially with n-butanol and diethyl ether
  5. customDrying under high vacuum

Sources & evidence

ORD record
ord-b1c9a8684f6a40c595f707ca175ded46
Source dataset
uspto-grants-2006_01
Patent number
US06987115B2

Reaction notes

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