Hydrochloric Acid → Lamtidine

HRID 35068Notes

Reaction equation

HRID 35068 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]3OCCO3)[CH:13]=2)=[N:5][C:4]([NH2:23])=[N:3]1.Cl.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[BH4-].[Na+]>O1CCCC1.O>[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:13]=2)=[N:5][C:4]([NH2:23])=[N:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 4311764Sodium borohydrideHCID 543287691-methyl-N5-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

Product 1

HCID 71988Lamtidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-methyl-N5 -[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (106 mg) in tetrahydrofuran (2 ml) was stirred with 2N hydrochloric acid (0.2 ml) for 1/2 h at room temperature. The mixture was treated with piperidine (0.5 ml), stirred at room temperature for 1 h, and then treated with sodium borohydride (75 mg). After a further 1 h, the mixture was diluted with water, and extracted with ethyl acetate. The combined extracts were dried and evaporated in vacuo. The resulting oil was crystallised from a mixture of benzene and cyclohexane to yield the title compound (60 mg) m.p. 93°-4°. TLC silica (methanol:ammonia 80:1) Rf 0.5.

Workup

  1. waitAfter a further 1 h
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were dried
  4. customevaporated in vacuo
  5. customThe resulting oil was crystallised from a mixture of benzene and cyclohexane

Sources & evidence

ORD record
ord-89f52ca148d64185a61326fe7adee8c2
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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