(+-)-alpha-Methyltryptamine → HCID 21101318, compound

HRID 2375475Notes

Reaction equation

HRID 2375475 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[CH3:15][CH:16]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[NH2:17].C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=[C:2]([NH:17][CH:16]([CH3:15])[CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[N:7]=1

Participants

5

Reactant 3

HCID 9287(+-)-alpha-MethyltryptamineHCID 11430Potassium CarbonateHCID 211012992,4-Dichloro-6-(piperidin-1-yl)pyrimidine

Product 1

HCID 21101318HCID 21101318, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2,4-dichloro-6-(1-piperidinyl)pyrimidine (80 mg, 0.34 mmol), α-methyltryptamine (59 mg, 0.34 mmol), and potassium carbonate (47 mg, 0.34 mmol) in chlorobenzene (1 mL) was heated at 150° C. in a sealed tube for 16 hours. The solvent was removed and the crude material was purified by preparative TLC, eluting with cyclohexane/ethyl acetate (4:1). 4-Chloro-N-[2-(1H-indol-3-yl)-1-methylethyl]-6-(1-piperidinyl)-2-pyrimidinamine (Rf=0.19) was obtained as a solid (64.5 mg, 51%). 1H NMR (300 MHz, CDCl3) δ 8.29 (br s, 1H), 7.68 (br d, 1H, J=7.5), 7.32 (d, 1H, J=7.8), 7.16 (t, 1H, J=7.8), 7.12 (t, 1H, J=7.8), 6.95 (d, 1H, J=2.1), 5.87 (s, 1H), 4.89 (br d, 1H, J=8.1), 4.36 (sextet, 1H, J=6.6), 3.58-3.50 (m, 4H), 3.07 (dd, 1H, J=14.4, 5.1), 2.83 (dd, 1H, J=14.1, 7.2), 1.70-1.55 (m, 6H), 1.16 (d, 3H, J=6.6).

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by preparative TLC
  3. washeluting with cyclohexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-863a2e0c6c404e9d8a9e40502dadc7ff
Source dataset
uspto-grants-2008_12
Patent number
US07465750B2

Reaction notes

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