Hydrochloric Acid → 6-Morpholino-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

HRID 1618501Notes

Reaction equation

HRID 1618501 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]3[N:13](C(=O)C)[CH2:14][C:15]4([CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:10]3=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl>C(#N)C>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[CH:12]=[C:11]3[NH:13][CH2:14][C:15]4([CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:10]3=[CH:9][CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 672850401-(6-Morpholino-2',3',5',6'-tetrahydrospiro-[indoline-3,4'-pyran]-1-yl)ethanone

Product 1

HCID 672846616-Morpholino-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(6-morpholino-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone (1.35 g, 4.27 mmol) in acetonitrile (30 mL) was treated with 2.0M aqueous HCl (12 mL). The reaction was stirred at rt overnight and then it was heated to 120° C. for 36 h. After this time the reaction was cooled to rt and quenched with aqueous NaOH. The mixture was partitioned between EtOAc (200 mL) and water (80 mL). The separated organic layer was washed with NaHCO3 (saturated aqueous solution) and then it was dried over MgSO4, filtered and evaporated in vacuo to give 6-morpholino-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] as a pale solid. Mass Spectrum (ESI) m/e=275 (M+1).

Workup

  1. temperatureit was heated to 120° C. for 36 h
  2. temperatureAfter this time the reaction was cooled to rt
  3. customquenched with aqueous NaOH
  4. customThe mixture was partitioned between EtOAc (200 mL) and water (80 mL)
  5. washThe separated organic layer was washed with NaHCO3 (saturated aqueous solution)
  6. dry with materialit was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-62c63346ed534874b3cdc3d8545af754
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

Loading…