Acetic Acid → N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

HRID 1024486

Reaction equation

HRID 1024486 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH:13]=O)[CH:3]=1.[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:19][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6558IsobutylamineHCID 49622469-chloro-3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To an ice cold mixture of 9-chloro-3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde (2.07 g) and of isobutylamine (7.5 ml 8 eq.) were combined in 1,2-dichloroethane (75 ml) and cooled in ice water bath. Acetic acid (5.68 ml) was then added and followed by sodium triacetoxyborohydride (2.75 g, 1.4 eq.). The mixture was allowed to stir at room temperature overnight. It was partitioned with aqueous K2CO3 (75 mL, 1.5M). The aqueous layer was extracted with of dichloromethane (75 ml×2). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by flash column chromatography (10-100% ethyl acetate in hexanes) gave the desired amine as a light yellow oil: MS (m+1)=270.2.

Workup

  1. customIt was partitioned with aqueous K2CO3 (75 mL, 1.5M)
  2. extractionThe aqueous layer was extracted with of dichloromethane (75 ml×2)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (10-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-aec57fd526534ee0a281ac98e20cf341
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Linked notes

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