Formaldehyde → N,N-Dimethyltryptamine

HRID 1450499Notes

Reaction equation

HRID 1450499 reaction equation
C=O.CN1N=NC(C[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[CH2:19][CH2:20]N)=N1.[BH3-][C:23]#[N:24].[Na+].[C:26]([O-])([O-])=O.[K+].[K+]>CO.C(O)(=O)C>[CH3:26][N:24]([CH3:23])[CH2:20][CH2:19][C:13]1[C:12]2[C:16](=[CH:17][CH:18]=[CH:10][CH:11]=2)[NH:15][CH:14]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 10060971HCID 10060971, compound

Product 1

HCID 6089N,N-DimethyltryptamineYield 87%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

A solution of formaldehyde (80 mg of a 30% solution) in methanol (15 ml) was added to a stirred solution of 2-[5-(2-methyltetrazol-5-ylmethyl)-1H-indol-3-yl]etylamine (0.1 g, 0.4 mmol), NaCNBH3 (60 mg) and glacial acetic acid (0.12g) in methanol (15 ml). The solution was stirred for 2 h, basified with K2CO3 solution and the MeOH removed under vacuum. The crude product obtained after extraction into ethylacetate and removal of solvent was chromatographed through silica-gel eluting with CH2Cl2 /EtOH/NH3 (40:8:1) to give the desired N,N-dimethyltryptamine (96 mg, 87%). The oxalate salt was prepared: mp 185°-187° C. (MeOH/Et2O); (Found: C, 54.42; H, 5.74; N, 22.53. C15H20N6. C2H2O4 requires C, 54.54; H, 5.92; N, 22.45%); δ (360 MHz, D2O) 2.91 (6H, s, 2 of CH3); 3.21 (2H, t, J=7.4 Hz, CH2); 3.47 (2H, t, J=7.4 Hz, CH2); 4.30 (3H, s, CH3); 4.34 (2H, s, CH2); 7.17 (1H, dd, J=1.5 and 8.4 Hz, Ar--H); 7.33 (1H, s, Ar--H); 7.48 (1H, d, J=8.4 Hz, Ar--H); 7.59 (1H, s, Ar--H).

Workup

  1. customthe MeOH removed under vacuum
  2. customThe crude product obtained
  3. extractionafter extraction
  4. custominto ethylacetate and removal of solvent
  5. customwas chromatographed through silica-gel
  6. washeluting with CH2Cl2 /EtOH/NH3 (40:8:1)

Sources & evidence

ORD record
ord-463ec6a34ab84f619c6e8050f667c0b0
Source dataset
uspto-grants-1997_02
Patent number
US05602163

Reaction notes

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