1-Bromopropane → 1-(3-Chlorophenoxy)-3-propyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 414807Notes

Reaction equation

C(O)(=O)C(O)=O.[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][NH:14][CH2:13]1.Br[CH2:27][CH2:28][CH3:29].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][CH2:15][N:14]([CH2:27][CH2:28][CH3:29])[CH2:13]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-(m-chlorophenoxy)-2,3,4,5-tetrahydro-3-benzazepine of Example 4 (6.4 g, 0.023 mole), 1-bromopropane (5.7 g., 0.047 mole) and sodium bicarbonate (8.4 g, 0.10 mole) in DMF (100 ml) was stirred at 70° C. for three hours. The mixture was concentrated under high vaccum to an oil which was stirred with water then extracted with ether. The ether extracts were washed twice with water and dried (saturated NaCl, anhydrous MgSO4). The solution was filtered, then concentrated to an oil (6.3 g, 86%) which was distilled to yield an oil of 1-(m-chlorophenoxy)-3-(n-propyl)-2,3,4,5-tetrahydro-3-benzazepine, 190°-210° C./0.1 mm.

Workup

concentrationThe mixture was concentrated under high vaccum to an oil which
stirringwas stirred with water
extractionthen extracted with ether
washThe ether extracts were washed twice with water
dry with materialdried (saturated NaCl, anhydrous MgSO4)
filtrationThe solution was filtered
concentrationconcentrated to an oil (6.3 g, 86%) which
distillationwas distilled

Sources & evidence

ORD record: ord-0874d09e2191440a8a030f46a5470a98
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04794181

Reaction notes

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