Acetic Acid → HCID 15839989, compound

HRID 1739807Notes

Reaction equation

HRID 1739807 reaction equation
Cl.[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[NH2:11].C(N(CC)CC)C.[O:19]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([N:29]3[CH2:34][CH2:33][C:32](=O)[CH2:31][CH2:30]3)[C:23]=2[S:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl>[O:19]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([N:29]3[CH2:34][CH2:33][CH:32]([NH:11][CH:3]4[CH2:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH2:2]4)[CH2:31][CH2:30]3)[C:23]=2[S:22][CH2:21][CH2:20]1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 1227642-Aminoindan hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 21837540HCID 21837540, compound

Product 1

HCID 15839989HCID 15839989, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

0.17 g (1 mmol) of indan-2-ylamine hydrochloride is introduced into 7 ml of 1,2-dichloroethane and then, in order, 0.14 ml (1.5 mmol) of triethylamine, 0.25 g of 1-(2,3-dihydro[1,4]benzoxathiin-5-yl)piperid-4-one (Preparation 4), 0.32 g (1.5 mmol) of sodium triacetoxyborohydride and 58 μl (1 mmol) of acetic acid are added. The whole is stirred for 20 hours at room temperature and then poured into 10 ml of 1N sodium hydroxide solution and extracted twice with 25 ml of ether each time. The combined organic phases are washed and dried. Evaporation yields 0.36 g of the title product, which is converted into the hemifumarate by the action of a 2% solution of fumaric acid in ethanol. In that manner, 0.27 g of hemifumarate is obtained. M.p. (MK)=220-223° C.

Workup

  1. extractionextracted twice with 25 ml of ether each time
  2. washThe combined organic phases are washed
  3. customdried
  4. customEvaporation

Sources & evidence

ORD record
ord-69db58d8ad0c4c08b941157638c1fc61
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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