Ammonia → HCID 13691208, compound

HRID 1721948Notes

Reaction equation

HRID 1721948 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16](O)[CH:17]=[CH:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[CH:21]=[CH:22][NH:23]2)([CH3:4])[CH3:3].N.[Cl-].[NH4+]>O1CCCC1>[NH:23]1[C:24]2[C:20](=[C:19]([CH2:18][CH2:17][CH2:16][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][CH2:8][CH2:7][CH2:6][NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])[CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:22]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 54454445HCID 54454445, compound

Product 1

HCID 13691208HCID 13691208, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.38 g of the product of Example 6 and 25 ml of tetrahydrofuran was added at -78° C. to 30 ml of ammonia and after adding 3 g of sodiunm at -40° C., the mixture was stirred for 90 minutes under an inert atmosphere. 24 g of ammonium chloride were added at -40° C. and the ammonia evaporated. The residue was diluted with water and the mixture was extracted with ethyl acetate. The organic phase was washed with water, aqueous sodium chloride, dried over a deshydrant, filtered and evaporated to dryness to obtain 2.86 g of N-[3-{2-(3-[1H-indol-4-yl]-propyl)-phenoxy}-propyl]2-methyl-2-propanamine.

Workup

  1. additionafter adding 3 g of sodiunm at -40° C.
  2. customthe ammonia evaporated
  3. additionThe residue was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with water, aqueous sodium chloride
  6. customdried over a deshydrant
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-0b2601fa06384efcaec7fb7ef86368fa
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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