Ammonia → HCID 58932538, compound

HRID 853868Notes

Reaction equation

HRID 853868 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[C:7]2([O:19][CH2:18][CH2:17][CH2:16][O:15]2)[C:6]1=O.N>CCO>[Br:14][C:10]1[CH:11]=[CH:12][C:13]2[N:5]3[CH2:4][CH2:3][CH2:2][N:1]=[C:6]3[C:7]3([O:19][CH2:18][CH2:17][CH2:16][O:15]3)[C:8]=2[CH:9]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 58932582HCID 58932582, compound

Product 1

HCID 58932538HCID 58932538, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1′-(3-aminopropyl)-5′-bromospiro[1,3-dioxane-2,3′-indol]-2′(1′H)-one (1.89 g, 5.54 mmol) in 2M EtOH.NH3 (150 mL) was heated in a steel pressure vessel at 135° C. for 46 hr. After cooling to room temperature the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluting with 85/15 Pet ether/acetone to give the title compound (0.84 g, 66% ). A portion was dried in vacuo at 50° C. to give the analytically pure sample. Anal: Calc'd for C14H15BrN2O2: C, 52.03; H, 4.68; N, 8.67. Found: C, 52.10; H, 4.63; N 8.46. IR: consistent, NMR (300 Mz, DMSO-d6): consistent. MS: (ESI+) m/z 323 [M+H], 1 Br pattern observed. m.p.: 145-149° C.

Workup

  1. concentrationwas concentrated
  2. customThe crude product was purified on Biotage KP silica gel eluting with 85/15 Pet ether/acetone

Sources & evidence

ORD record
ord-2f220e2281194ae89fffae00edbaf00c
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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