HCID 13472779, compound → HCID 13472846, compound

HRID 1248183Notes

Reaction equation

HRID 1248183 reaction equation
C[O:2][C:3]1[C:12]2[CH2:11][N:10]([CH3:13])[CH2:9][CH:8]3[C:14]4[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=4[CH2:16][CH2:17][C:6]([C:7]=23)=[CH:5][C:4]=1[O:22][CH3:23]>I>[CH3:23][O:22][C:4]1[C:3]([OH:2])=[C:12]2[C:7]3[CH:8]([C:14]4[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=4[CH2:16][CH2:17][C:6]=3[CH:5]=1)[CH2:9][N:10]([CH3:13])[CH2:11]2

Participants

3

Reactant 1

HCID 13472779HCID 13472779, compound

Product 1

HCID 13472846HCID 13472846, compound

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

A suspension of the di(lower)alkoxy compound, 4,5-dimethoxy-2-methyl-1,2,3,7,8,12b-hexahydrobenzo[6,7]cyclohepta[1,2,3-de]isoquinoline (1.0 g, 3.2 mmol, described in example 4) in 58% (v/w) hydriodic acid (30 mL) was stirred in a closed vessel for 3 weeks at 20°-22° C. The reaction mixture was poured into ice water (50 mL). The resulting precipitate was collected, washed with a small amount of water, and then partitioned between concentrated ammonium hydroxide-water (1:1, v/v) and ethyl acetate. The organic phase was separated, washed with brine, dried (MgSO4) and evaporated to dryness to give the title compound as a yellow solid. The product was purified by converting it to its hydrochloride and then regenerating the free base (0.864 g) from the hydrochloride. When purified in this manner and recrystallized from chloroform-hexane, the title compound had mp 173°-174° C.; NMR (CDCl3) δ2.50 (s, 3H), 3.75 (s, 3H), 4.55 (m, 1H), 5.50 (broad, 1H), 6.34 (s, 1H), 7.10 (m, 3H), 7.50 (m, 1H); Anal Calcd for C19H21NO2 : C, 77.26% H, 7.17% N, 4.74%; Found: C, 77.36% H, 7.23% N, 4.68%.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with a small amount of water
  3. custompartitioned between concentrated ammonium hydroxide-water (1:1
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9dc0d0ba1ca64a26b47d827af2a40c21
Source dataset
uspto-grants-1985_06
Patent number
US04522946

Reaction notes

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