1,1-Dichloroethane → HCID 58550854, compound

HRID 1907996Notes

Reaction equation

HRID 1907996 reaction equation
[N:1]1([C:6]2[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.O=[C:14]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]1.O.CC1C=CC(S(O)(=O)=O)=CC=1.ClC(Cl)C>>[N:7]1[C:6]2[N:1]3[CH:2]=[CH:3][CH:4]=[C:5]3[C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 10583088HCID 10583088, compound

Product 1

HCID 58550854HCID 58550854, compoundYield 93%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-pyrrol-1-ylpyridin-3-ol (1.00 g, 6.24 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (1.24 g, 6.24 mmol), 4-methylbenzenesulfonic acid hydrate (119 mg, 0.625 mmol), molecular sieves (442 mg) and dichloroethane (8.9 mL) was heated at 130° C. for 162 hours. The reaction was filtered and washed with dichloroethane. The solid was dissolved in MeOH and filtered through a plug of Celite. The solvent was evaporated under reduced pressure to yield spiro[piperidine-4,6′-pyrido[3,2-b]pyrrolo[1,2-d][1,4]oxazine] (1.4 g, 38%). ESI-MS m/z calc. 241.1. found 242.5 (M+1)+; Retention time: 1.10 minutes (4 min run).

Workup

  1. filtrationThe reaction was filtered
  2. washwashed with dichloroethane
  3. dissolutionThe solid was dissolved in MeOH
  4. filtrationfiltered through a plug of Celite
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d9778bf479944affbeb94e9350254cf1
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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