Ammonia → HCID 20270309, compound

HRID 485394Notes

Reaction equation

HRID 485394 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8](=O)[CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:14]=2)=[N:5][C:4]([C:27](OC)=O)=[N:3]1.[NH3:31]>>[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:14]=2)=[N:5][C:4]([CH2:27][NH2:31])=[N:3]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 20270304HCID 20270304, compound

Product 1

HCID 20270309HCID 20270309, compound

Procedure

A solution of methyl 1-methyl-5-[[1-oxo-4-[3-(1-piperidinylmethyl)phenoxy]butyl]amino]-1H-1,2,4-triazole-3-carboxylate (1.94 g) in 0.88 ammonia was stirred at room temperature for 18 h. The mixture was evaporated to yield a yellow foam, which was triturated with ether to give a yellow solid (1.56 g) which was used without further purification. A portion of this solid (1.20 g) was suspended in tetrahydrofuran (50 ml) and treated at room temperature with lithium aluminium hydride (1.0 g). The mixture was heated under reflux for 24 h, cooled and quenched with water. The resulting mixture was extracted with ethyl acetate, and the combined organic extracts were evaporated to yield an oil (0.90 g) which was chromatographed to give the title compound as an oil (210 mg).

Workup

  1. customThe mixture was evaporated
  2. customto yield a yellow foam, which
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-c3e567cd62964097b0ec8987792b08e8
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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