Water → HCID 23467211, compound

HRID 443430Notes

Reaction equation

HRID 443430 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[C:7]1([CH:13]2[CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26][N:21]3[C:15]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[O:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH:1]1([C:4]([N:18]2[CH2:19][CH2:20][C:15]3([N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]4[CH:13]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:14]3)[CH2:16][CH2:17]2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 23467217HCID 23467217, compound

Product 1

HCID 23467211HCID 23467211, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The hexahydro-1'-(cyclopropylcarbonyl)-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-pipridine] used as the starting material in the above procedure can be prepared by the following procedure. Cyclopropanecarboxylic acid chloride, 2 g, is added dropwise to a stirred solution of 4 g of hexahydro-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine] and 2.8 ml of triethylamine in 100 ml of methylene dichloride at 50° C. the reaction mixture is allowed to stand at room temperature overnight and then stirred with 75 ml of water. The organic layer is separated, washed with a saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate and evaporated to dryness. The residual oil is crystallized from 30 ml of cyclohexane to obtain 4.2 g of hexahydro-1'-(cyclopropylcarbonyl)-1-phenylspiro[3H-oxazolo[3,4-a]pyridine-3,4'-piperidine]; mp 110°-114° C.

Workup

  1. customcan be prepared by the following procedure
  2. customThe organic layer is separated
  3. washwashed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe residual oil is crystallized from 30 ml of cyclohexane

Sources & evidence

ORD record
ord-7c83cc42c83841159ee2ea1f3dd797e4
Source dataset
uspto-grants-1981_04
Patent number
US04260623

Reaction notes

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