1,2-Dichloroethane → HCID 58551616, compound

HRID 1908151Notes

Reaction equation

HRID 1908151 reaction equation
[OH:1][C:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[O:14][CH3:15])([CH3:4])[CH3:3].[CH:16]1[N:24]2[C:19]([C:20]3([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[O:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=32)=[CH:18][CH:17]=1.C(N(CC)CC)C.C(Cl)CCl>C(Cl)Cl>[OH:1][C:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([N:31]2[CH2:30][CH2:29][C:20]3([O:21][C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[N:24]4[CH:16]=[CH:17][CH:18]=[C:19]34)[CH2:33][CH2:32]2)=[O:11])=[CH:7][C:6]=1[O:14][CH3:15])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 58550727Spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]HCID 585509664-(2-Hydroxypropan-2-yl)-3-methoxybenzoic acid

Product 1

HCID 58551616HCID 58551616, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-benzoic acid (120 mg, 0.573 mmol), spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine] (167 mg, 0.573 mmol), triethylamine (320 μL, 2.29 mmol), and EDC (110 mg, 0.573 mmol) were combined in DCM (5.8 mL). The reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was washed three times with a 1M solution of hydrochloric acid, followed by three washes with a saturated aqueous solution of sodium bicarbonate, followed by three washes of a saturated aqueous solution of sodium chloride. The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness to provide (4-(2-hydroxypropan-2-yl)-3-methoxyphenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone. ESI-MS m/z calc. 432.0. found 433.1 (M+1)+; Retention time: 1.61 minutes (3 min run).

Workup

  1. washThe reaction mixture was washed three times with a 1M solution of hydrochloric acid
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5e81491317ff4f218080d1e18fc1e0eb
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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