Hydroxyamine hydrochloride → 1-benzyl-4-chloro-5-hydroxyiminomethyl-2,3,6,7-tetrahydro-1H-azepine

HRID 1364111Notes

Reaction equation

HRID 1364111 reaction equation
[Cl:1][C:2]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][C:3]=1[CH:16]=O.Cl.[NH2:19][OH:20]>C(O)C>[Cl:1][C:2]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][C:3]=1[CH:16]=[N:19][OH:20]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 130720301-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde

Product 1

HCID 866216731-benzyl-4-chloro-5-hydroxyiminomethyl-2,3,6,7-tetrahydro-1H-azepine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-chloro-1-(phenylmethyl)-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde (may be prepared as described in Description 3) (11.6 g, 46.5 mmol) in ethanol (100 ml) was stirred with hydroxylamine hydrochloride (3.23 g, 46.5 mmol) at room temperature for 72 hours. The ethanol was removed by evaporation and the residue partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The ethyl acetate was washed with water & brine, then dried and evaporated to afford the title compound (D4); MS (ES+) m/e 265 & 267 [M+H]+.

Workup

  1. customThe ethanol was removed by evaporation
  2. customthe residue partitioned between ethyl acetate
  3. washThe ethyl acetate was washed with water & brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f6343538d864474eb30118734b8d5902
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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