Triethylamine → HCID 10476225, compound

HRID 2164671Notes

Reaction equation

HRID 2164671 reaction equation
[CH:1]([NH:4][CH2:5][CH:6]1[CH2:10][O:9][C:8]2([CH:18](Br)[CH2:17][CH2:16][C:15]3[N:14]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:13]=[CH:12][C:11]2=3)[O:7]1)([CH3:3])[CH3:2].C(N(CC)CC)C>ClCCl>[OH:7][CH:6]([CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])[CH2:10][O:9][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[S:20]([C:23]1[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 12946401HCID 12946401, compound

Product 1

HCID 10476225HCID 10476225, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4'-isopropylaminomethyl-5-bromo-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane (100 parts) and triethylamine (143 parts) in dichloromethane (1500 parts) is dropwise added a solution of stannic chloride (80 parts) in dichloromethane (500 parts) at -60° C. with stirring. The mixture is warmed to room temperature, stirred for 5 hours, concentrated and shaken with aqueous 5N-sodium hydroxide and ethyl acetate. The ethyl acetate layer is separated, washed with water, dried over sodium sulfate and concentrated under reduced pressure to give crude product (73 parts) in 87.9% yield. This is triturated in ethyl acetate to give pure 4-(2-hydroxy-3-isopropylaminopropoxy)-1-p-toluenesulfonylindole (56.1 parts) as amorphous solid in 67% yield. NMR: δCD 3SOCD 3 0.97d(6.5 Hz)6H, 2.29s3H, 2.56-2.90m3H, 3.76-4.20m3H, 6.71-7.92m9H. (HCl salt of the product) m.p. 225°-226° C. (decomp.). NMR: δCD 3SOCD 3 1.28d(6.5 Hz)6H, 2.29s3H, 2.76-3.58m, 3.93-4.53m3H, 5.92brs1H, 6.73-7.00m2H, 7.15-7.96m7H, 9.09brs2H. (HBr salt of the product) m.p. 235°-238° C. (decomp.). (HI salt of the product) m.p. 227.5° C. (decomp.)

Workup

  1. stirringstirred for 5 hours
  2. concentrationconcentrated
  3. stirringshaken with aqueous 5N-sodium hydroxide and ethyl acetate
  4. customThe ethyl acetate layer is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give crude product (73 parts) in 87.9% yield
  9. customThis is triturated in ethyl acetate

Sources & evidence

ORD record
ord-10bf5bd2f60e4789a31fc84282b03b43
Source dataset
uspto-grants-1985_03
Patent number
US04506079

Reaction notes

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