Acetic Acid → HCID 10221947, compound

HRID 1179044Notes

Reaction equation

HRID 1179044 reaction equation
[CH3:1][CH:2]([NH2:13])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.Cl.[CH2:15]([C:22]1([N:36]([CH3:38])[CH3:37])[CH2:27][CH2:26][CH:25](NCC2C=CC=CC=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O>[CH2:15]([C:22]1([N:36]([CH3:37])[CH3:38])[CH2:27][CH2:26][CH:25]([NH:13][CH:2]([CH3:1])[CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 9287(+-)-alpha-MethyltryptamineHCID 5049666Sodium triacetoxyborohydrideHCID 69337492HCID 69337492, compound

Product 1

HCID 10221947HCID 10221947, compoundYield 152.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

348 mg DL-α-methyltryptamine were dissolved in dry 1,2-dichloroethane (10 ml) under argon (clear solution), 463 mg 4-benzyl-4-dimethylamino-cyclohexane (see example 3) and glacial acetic acid (229 μl) were added and the mixture was stirred for one hour at RT. 550 mg sodium triacetoxyborohydride were then added and the suspension was stirred for a further 72 hours at RT. For working up, water (20 ml) was added to the reaction mixture, the organic phase was separated off and the aqueous phase was extracted once with ether and then rendered strongly alkaline with sodium hydroxide solution (pH>10). A gelatinous precipitate which dissolved in ethyl acetate thereby precipitated out. The aqueous phase was extracted with ethyl acetate (4×10 ml). All the ethyl acetate phases were combined, dried with sodium sulfate and concentrated to dryness. 766 mg of a mixture of cis- and trans-1-benzyl-N′-[2-(1H-indol-3-yl)-1-methylethyl]-N,N-dimethylcyclohexane-1,4-diamine were obtained as a vitreous solid (m.p. 48-53° C.).

Workup

  1. stirringthe suspension was stirred for a further 72 hours at RT
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted once with ether
  4. dissolutionA gelatinous precipitate which dissolved in ethyl acetate
  5. customthereby precipitated out
  6. extractionThe aqueous phase was extracted with ethyl acetate (4×10 ml)
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9c5b0d5222b8422cba93b896a2901dc7
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

Loading…